Dichloromethane → Morpholine

HRID 1966389

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[O:10])=[CH:4][CH:3]=1.CCN(CC)CC.C(Cl)[Cl:25]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([Cl:25])=[O:10])=[CH:4][CH:3]=1.[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1

Participants

Reactant 3

HCID 6344Dichloromethane

HCID 8471Triethylamine

HCID 8758802-(4-Bromophenyl)-1-morpholinoethanone

Product 2

HCID 8083Morpholine

HCID 181552Benzeneacetyl chloride, 4-bromo-

Procedure

The compound shown on the left above, 2-(4-bromo-phenyl)-1-morpholin-4-yl-ethanone, is obtained by reaction of the corresponding acid chloride (A), (4-bromo-phenyl)-acetyl chloride, with morpholine and Et3N in DCM at rt. The product is obtained in high yield. The intermediate acid chloride (A) is obtained by reaction of (4-bromo-phenyl)-acetic acid (B) and oxalyl chloride (C) in DCM at rt and using DMF as reaction initiator. The intermediate (A) is obtained in good yield.

Sources & evidence

ORD record: ord-9280a041ff484844a75c851808f0414b
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420657B2

Linked notes

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