Cyclopropylamine → N-cyclopropyl-3,4-difluorobenzamide

HRID 69709

Reaction equation

[CH:1]1([NH2:4])[CH2:3][CH2:2]1.[F:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][C:14]=1[F:15])[C:9](O)=[O:10]>>[CH:1]1([NH:4][C:9](=[O:10])[C:8]2[CH:12]=[CH:13][C:14]([F:15])=[C:6]([F:5])[CH:7]=2)[CH2:3][CH2:2]1

Participants

Reactant 2

HCID 69828Cyclopropylamine

HCID 991663,4-Difluorobenzoic acid

Product 1

HCID 17683018N-cyclopropyl-3,4-difluorobenzamideYield 89%

Procedure

Using cyclopropylamine and 3,4-difluorobenzoic acid in the general procedure for coupling of amines to carboxylic acids, the title compound was obtained (89% yield) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.52-0.63 (m, 2 H) 0.63-0.74 (m, 2 H) 2.83 (tq, J=7.42, 3.98 Hz, 1 H) 7.52 (dt, J=10.55, 8.37 Hz, 1 H) 7.66-7.75 (m, 1 H) 7.85 (ddd, J=11.68, 7.89, 2.15 Hz, 1 H) 8.42-8.60 (m, 1 H). ESI-MS: m/z 198.1 (M+H)+. mp=104.1-108.4° C.

Sources & evidence

ORD record: ord-e833bf13b64e4a2091f431076aaffdf0
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822470B2

Linked notes

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