Benzenemethanamine, 3-chloro- → HCID 53323535, compound

HRID 2106183Notes

Reaction equation

HRID 2106183 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:29]=[C:30]([CH:33]=[CH:34][CH:35]=1)[CH2:31]N>>[Cl:27][C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][CH:35]=1)[CH2:31][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 77802Benzenemethanamine, 3-chloro-HCID 95339p-Chloro-beta-nitrostyreneHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 53323535HCID 53323535, compound

Procedure

The title compound (212.8 mg) was prepared from 0.55 g of 4-oxo-piperidine-1-carboxylic acid tert-butyl ester, 340 μL of 3-chlorobenzylamine, and 0.51 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): 7.38-7.28 (m, 6H), 7.18-7.15 (m, 2H), 7.12-7.09 (m, 1H), 5.16 (s, 2H), 4.36 (s, 2H), 3.52 (t, J=6.3 Hz, 2H), 2.86 (t, J=6.3 Hz, 2H).

Workup

  1. customwith crushed 4 Å molecular sieves

Sources & evidence

ORD record
ord-5081ff63325e400485f09f00d9206318
Source dataset
uspto-grants-2009_08
Patent number
US07579470B2

Reaction notes

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