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

HRID 2106186Notes

Reaction equation

HRID 2106186 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.[Cl:23][C:24]1[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:25]=1[CH:31]=[CH:32][N+]([O-])=O>CCO.C1(C)C=CC=CC=1>[CH2:15]([N:22]1[C:11]2[CH2:10][CH2:9][NH:8][CH2:13][C:12]=2[C:31]([C:25]2[CH:26]=[CH:27][C:28]([Cl:30])=[CH:29][C:24]=2[Cl:23])=[CH:32]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 2558822,4-DichloronitrostyreneHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 533231861-benzyl-3-(2,4-dichlorophenyl)-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine

Reagents, catalysts & solvents 1

HCID 21863594Toluene ethanolSolvent

Procedure

The title compound (454.6 mg) was prepared from 0.52 g of 4-oxo-piperidine-1-carboxylic acid tert-butyl ester, 280 μL of benzylamine, and 0.57 g of 2,4-dichloro-1-(2-nitro-vinyl)-benzene, using a 5:1 EtOH/toluene mixture as the solvent. MS (ESI): exact mass calculated for C20H18Cl2N2, 356.08; found, m/z 357.1 [M+H]+. 1H NMR (500 MHz, CD3OD): 7.53 (d, J=2.2 Hz, 1H), 7.36-7.32 (m, 3H), 7.30-7.28 (m, 2H), 7.20-7.17 (m, 2H), 7.04 (s, 1H), 5.16 (s, 2H), 4.13 (s, 2H), 3.50 (t, J=6.3 Hz, 2H), 2.88 (t, J=6.3 Hz, 2H).

Sources & evidence

ORD record
ord-0695eec6115a4c7ea12686b935c07933
Source dataset
uspto-grants-2009_08
Patent number
US07579470B2

Reaction notes

Loading…