Benzylamine → 1-Benzyl-3-(4-trifluoromethyl-phenyl)-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine

HRID 599888Notes

Reaction equation

HRID 599888 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)=O)(C)(C)C.[CH2:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[F:23][C:24]([F:37])([F:36])[C:25]1[CH:30]=[CH:29][C:28]([CH:31]=[CH:32][N+]([O-])=O)=[CH:27][CH:26]=1>C(#N)C>[CH2:15]([N:22]1[C:11]2[CH2:10][CH2:9][NH:8][CH2:13][C:12]=2[C:31]([C:28]2[CH:29]=[CH:30][C:25]([C:24]([F:23])([F:36])[F:37])=[CH:26][CH:27]=2)=[CH:32]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 6882311-(2-Nitro-vinyl)-4-trifluoromethyl-benzeneHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 533227591-Benzyl-3-(4-trifluoromethyl-phenyl)-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound (0.23 g) was prepared from 0.50 g of 4-oxo-piperidine-1-carboxylic acid tert-butyl ester, 274 μL of benzylamine, and 0.55 g of 1-trifluoromethyl-4-(2-nitro-vinyl)-benzene, using acetonitrile as the solvent. MS (ESI): exact mass calculated for C21H19F3N2, 356.16; m/z found, 357.2 [M+H]+. 1H NMR (500 MHz, CD3OD): 7.65-7.63 (m, 2H), 7.54-7.52 (m, 2H), 7.36-7.27 (m, 4H), 7.20-7.18 (m, 2H), 5.17 (s, 2H), 4.40 (s, 2H), 3.52 (t, J=6.3 Hz, 2H), 2.88 (t, J=6.3 Hz, 2H).

Sources & evidence

ORD record
ord-a109a952b108484c82e317db8662c3a2
Source dataset
uspto-grants-2011_03
Patent number
US07897771B2

Reaction notes

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