4-Methoxybenzylamine → 2-[[(4-Methoxyphenyl)methyl]amino]-3-pyridinecarbonitrile

HRID 1663084Notes

Reaction equation

Cl[C:2]1[N:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH3:10][O:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][NH2:17])=[CH:14][CH:13]=1.C(N(CC)C(C)C)(C)C>CC(O)C>[CH3:10][O:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][NH:17][C:2]2[N:9]=[CH:8][CH:7]=[CH:6][C:3]=2[C:4]#[N:5])=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred mixture of 2-chloro-nicotinonitrile (Aldrich, 2.20 g, 15.88 mmol) and 4-methoxy-benzylamine (2.27 ml, 17.49 mmol) in 2-propanol (20 ml) was added N,N-diisopropylethylamine (5.53 ml, 31.75 mmol). The reaction mixture was heated to 80° C. and stirred at this temperature for 24 hours. More 4-methoxybenzylamine (0.50 ml, 3.85 mmol) was added and stirring continued at 70° C. for 48 hours. The mixture was cooled to room temperature and the resulting solid material (4-methoxy-benzylamine hydrochloride) removed by filtration. On standing a crystalline product formed in the filtrate, which was isolated by filtration, washed with 2-propanol and dried under reduced pressure affording the title compound as pale yellow crystals (1.27 g). 1H-NMR (DMSO-d6) δ 8.21-8.30 (m, 1H), 7.90 (d, 1H), 7.65 (t, 1H), 7.25 (d, 2H), 6.85 (d, 2H), 6.59-6.68 (m, 1H), 4.50 (d, 2H), 3.75 (s, 3H).

Workup

stirringstirring
waitcontinued at 70° C. for 48 hours
temperatureThe mixture was cooled to room temperature
customthe resulting solid material (4-methoxy-benzylamine hydrochloride) removed by filtration
customformed in the filtrate
customwhich was isolated by filtration
washwashed with 2-propanol
customdried under reduced pressure

Sources & evidence

ORD record: ord-6c7f78324fc1444b9e4f7cf0f6da2061
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08034811B2

Reaction notes

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