tert-Butyl 4-oxopiperidine-1-carboxylate → 1-Benzyl-3-(3-chloro-phenyl)-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine

HRID 2106205

Reaction equation

HRID 2106205 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)=O)(C)(C)C.[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH:22]=[CH:23][N+:24]([O-])=O)[CH:17]=1>C(N)C1C=CC=CC=1>[CH2:22]([N:24]1[C:11]2[CH2:10][CH2:9][NH:8][CH2:13][C:12]=2[C:22]([C:18]2[CH:19]=[CH:20][CH:21]=[C:16]([Cl:15])[CH:17]=2)=[CH:23]1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 27316461-Chloro-3-(2-nitroethenyl)benzene

Product 1

HCID 533166091-Benzyl-3-(3-chloro-phenyl)-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridineYield 48.9%

Reagents, catalysts & solvents 1

HCID 7504BenzylamineSolvent

Procedure

The title compound (193.3 mg) was prepared from 0.50 g of 4-oxo-piperidine-1-carboxylic acid tert-butyl ester, 260 μL of benzylamine, and 0.45 g of 1-chloro-3-(2-nitro-vinyl)-benzene as in Example 9. MS (ESI): exact mass calculated for C20H19ClN2, 322.12; found, m/z 323.2 [M+H]+. 1H NMR (500 MHz, CDCl3): 7.36-7.20 (m, 6H), 7.14-7.07 (m, 3H), 6.81 (s, 1H), 5.01 (s, 2H), 4.04 (s, 2H), 3.14 (t, J=5.8 Hz, 2H), 2.51 (t, J=5.8 Hz, 2H).

Sources & evidence

ORD record
ord-1847932f96434bdd94cb1066cb5f44e1
Source dataset
uspto-grants-2009_08
Patent number
US07579470B2

Linked notes

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