Cyclopropylamine → 3-chloro-N-cyclopropyl-4-fluorobenzamide

Reaction equation

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

Participants

Reactant 2

HCID 69828Cyclopropylamine

HCID 5209893-Chloro-4-fluorobenzoic acid

Product 1

HCID 583243603-chloro-N-cyclopropyl-4-fluorobenzamideYield 89%

Procedure

Using cyclopropylamine and 3-chloro-4-fluorobenzoic acid in the general procedure for coupling of amines to carboxylic acids, the title compound was obtained (89% yield) as a white solid. 1H NMR (DMSO-d6, 400 MHz): δ=8.56 (d, J=3.5 Hz, 1 H), 8.03 (dd, J=7.3, 2.3 Hz, 1 H), 7.85 (ddd, J=8.6, 4.8, 2.3 Hz, 1 H), 7.52 (t, J=9.0 Hz, 1 H), 2.83 (tq, J=7.4, 3.9 Hz, 1 H), 0.66-0.75 (m, 2 H), 0.53-0.61 ppm (m, 2 H). ESI-MS: m/z 214.0 (M+H)1.

Sources & evidence

ORD record: ord-a00e605506f7440fa81afe12dea55170
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822470B2

Reaction notes

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