2-Chlorobenzylamine → HCID 59752642, compound

HRID 749706Notes

Reaction equation

HRID 749706 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)=O)(C)(C)C.[N+:15]([CH:18]=[CH:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=1)([O-])=O.[Cl:27][C:28]1[CH:35]=[CH:34][CH:33]=[CH:32][C:29]=1[CH2:30]N>>[Cl:27][C:28]1[CH:35]=[CH:34][CH:33]=[CH:32][C:29]=1[CH2:30][N:15]1[C:11]2[CH2:10][CH2:9][NH:8][CH2:13][C:12]=2[C:19]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)=[CH:18]1

Participants

4

Reactant 3

HCID 666482-ChlorobenzylamineHCID 95339p-Chloro-beta-nitrostyreneHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 59752642HCID 59752642, compound

Procedure

The title compound (149.9 mg) was prepared from 0.50 g of 4-oxo-piperidine-1-carboxylic acid tert-butyl ester, 304 μL of 2-chlorobenzylamine, and 0.46 g of (2-nitro-vinyl)-4-chlorobenzene, replacing SiO2 with crushed 4 Å molecular sieves. MS (ESI): exact mass calculated for C20H18Cl2N2, 356.08; found, m/z 357.1 [M+H]+. 1H NMR (500 MHz, CD3OD): 7.58-7.56 (m, 1H), 7.47-7.45 (m, 1H), 7.37-7.26 (m, 5H), 7.10 (s, 1H), 6.85-6.82 (m, 1H), 5.25 (s, 2H), 4.38 (s, 2H), 3.53 (t, J=6.3 Hz, 2H), 2.88 (t, J=6.3 Hz, 2H).

Workup

  1. customwith crushed 4 Å molecular sieves

Sources & evidence

ORD record
ord-ba4b0264b4074793813dcd6b0c0c3fa5
Source dataset
uspto-grants-2008_07
Patent number
US07402680B2

Reaction notes

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