2-(4-Chlorophenyl)ethylamine → HCID 67153807, compound

HRID 714310Notes

Reaction equation

FC(F)(F)C1C=CC(CN)=CC=1.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][NH2:22])=[CH:16][CH:15]=1.[C:23]([NH:31][C:32]1[CH:33]=[C:34]([CH:38]=[CH:39][N:40]=1)[C:35](O)=[O:36])(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[C:23]([NH:31][C:32]1[CH:33]=[C:34]([CH:38]=[CH:39][N:40]=1)[C:35]([NH:22][CH2:21][CH2:20][C:17]1[CH:18]=[CH:19][C:14]([Cl:13])=[CH:15][CH:16]=1)=[O:36])(=[O:30])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

Reactant 3

HCID 674302-(4-Chlorophenyl)ethylamine

HCID 768044-(Trifluoromethyl)benzylamine

HCID 643938512-Benzamidoisonicotinic acid

Product 1

HCID 67153807HCID 67153807, compoundYield 52%

Procedure

Following the procedure as described in Example 1, making variations as required to replace (4-(trifluoromethyl)phenyl)methanamine with 2-(4-chlorophenyl)ethanamine to react with 2-benzamidoisonicotinic acid, 2-benzamido-N-[2-(4-chlorophenyl)ethyl]isonicotinamide was obtained as a colorless solid in 52% yield: 1H NMR (300 MHz, DMSO-d6) δ 10.97 (s, 1H), 8.82-8.05 (m, 1H), 8.54-8.49 (m, 2H), 8.06-8.04 (m, 2H), 7.63-7.46 (m, 4H), 7.38-7.27 (m, 4H), 3.51-3.49 (m, 2H), 2.86 (t, J=7.1 Hz, 2H); MS (ES+) m/z 380.4 (M+1), 382.3 (M+2).

Sources & evidence

ORD record: ord-373cef228bc740909a4ccad24742e37d
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187426B2

Reaction notes

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