A Solvent-Free Base Liberation of a Tertiary Aminoalkyl Halide by Flow Chemistry

Michael Jønch Pedersen; Tommy Skovby; Michael J. Mealy; Kim Dam-Johansen; Søren Kiil

doi:10.1021/acs.oprd.6b00223

A Solvent-Free Base Liberation of a Tertiary Aminoalkyl Halide by Flow Chemistry

Michael Jønch Pedersen, Tommy Skovby, Michael J. Mealy, Kim Dam-Johansen, Søren Kiil

H. Lundbeck A/S

Research output: Contribution to journal › Journal article › Research › peer-review

Abstract

A flow setup for base liberation of 3-(N,N-dimethylamino)propyl chloride hydrochloride and solvent-free separation of the resulting free base has been developed. Production in flow profits from an on-demand approach, useful for labile aminoalkyl halides. The requirement for obtaining a dry product has been fulfilled by the simple use of a saturated NaOH solution, followed by isolation of the liquid phases by gravimetric separation. The flow setup has an E factor reduction of nearly 50%, and a distillation step has been avoided. The method exemplifies how flow chemistry can be exploited to simplify, improve, and optimize manufacturing processes.

Original language	English
Journal	Organic Process Research & Development
Volume	20
Issue number	12
Pages (from-to)	2043-2049
ISSN	1083-6160
DOIs	https://doi.org/10.1021/acs.oprd.6b00223
Publication status	Published - 2016

Keywords

Acid−base reaction
Flow chemistry
Green chemistry

Access to Document

10.1021/acs.oprd.6b00223

OpenUrl availability

Full text

Cite this

@article{68e173405c9d45ebb705f452d06e3553,

title = "A Solvent-Free Base Liberation of a Tertiary Aminoalkyl Halide by Flow Chemistry",

abstract = "A flow setup for base liberation of 3-(N,N-dimethylamino)propyl chloride hydrochloride and solvent-free separation of the resulting free base has been developed. Production in flow profits from an on-demand approach, useful for labile aminoalkyl halides. The requirement for obtaining a dry product has been fulfilled by the simple use of a saturated NaOH solution, followed by isolation of the liquid phases by gravimetric separation. The flow setup has an E factor reduction of nearly 50%, and a distillation step has been avoided. The method exemplifies how flow chemistry can be exploited to simplify, improve, and optimize manufacturing processes.",

keywords = "Acid−base reaction, Flow chemistry, Green chemistry",

author = "Pedersen, {Michael J{\o}nch} and Tommy Skovby and Mealy, {Michael J.} and Kim Dam-Johansen and S{\o}ren Kiil",

year = "2016",

doi = "10.1021/acs.oprd.6b00223",

language = "English",

volume = "20",

pages = "2043--2049",

journal = "Organic Process Research & Development",

issn = "1083-6160",

publisher = "American Chemical Society",

number = "12",

}

TY - JOUR

T1 - A Solvent-Free Base Liberation of a Tertiary Aminoalkyl Halide by Flow Chemistry

AU - Pedersen, Michael Jønch

AU - Skovby, Tommy

AU - Mealy, Michael J.

AU - Dam-Johansen, Kim

AU - Kiil, Søren

PY - 2016

Y1 - 2016

N2 - A flow setup for base liberation of 3-(N,N-dimethylamino)propyl chloride hydrochloride and solvent-free separation of the resulting free base has been developed. Production in flow profits from an on-demand approach, useful for labile aminoalkyl halides. The requirement for obtaining a dry product has been fulfilled by the simple use of a saturated NaOH solution, followed by isolation of the liquid phases by gravimetric separation. The flow setup has an E factor reduction of nearly 50%, and a distillation step has been avoided. The method exemplifies how flow chemistry can be exploited to simplify, improve, and optimize manufacturing processes.

AB - A flow setup for base liberation of 3-(N,N-dimethylamino)propyl chloride hydrochloride and solvent-free separation of the resulting free base has been developed. Production in flow profits from an on-demand approach, useful for labile aminoalkyl halides. The requirement for obtaining a dry product has been fulfilled by the simple use of a saturated NaOH solution, followed by isolation of the liquid phases by gravimetric separation. The flow setup has an E factor reduction of nearly 50%, and a distillation step has been avoided. The method exemplifies how flow chemistry can be exploited to simplify, improve, and optimize manufacturing processes.

KW - Acid−base reaction

KW - Flow chemistry

KW - Green chemistry

U2 - 10.1021/acs.oprd.6b00223

DO - 10.1021/acs.oprd.6b00223

M3 - Journal article

SN - 1083-6160

VL - 20

SP - 2043

EP - 2049

JO - Organic Process Research & Development

JF - Organic Process Research & Development

IS - 12

ER -

A Solvent-Free Base Liberation of a Tertiary Aminoalkyl Halide by Flow Chemistry

Abstract

Keywords

Access to Document

OpenUrl availability

Fingerprint

Cite this