Beta-Nitrostyrene → HCID 53320865, compound

HRID 2106184Notes

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:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH2:18][NH2:19].[N+]([CH:27]=[CH:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([O-])=O>>[Cl:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH2:18][N:19]1[C:11]2[CH2:10][CH2:9][NH:8][CH2:13][C:12]=2[C:28]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:27]1

Participants

Reactant 3

HCID 7626Beta-Nitrostyrene

HCID 666482-Chlorobenzylamine

HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 53320865HCID 53320865, compound

Procedure

The title compound (113.8 mg) was prepared from 0.55 g of 4-oxo-piperidine-1-carboxylic acid tert-butyl ester, 334 μL of 2-chlorobenzylamine, 0.40 g of (2-nitro-vinyl)-benzene, and without SiO2. MS (ESI): exact mass calculated for C20H19ClN2, 322.12; found, m/z 323.2 [M+H]+. 1H NMR (500 MHz, CD3OD): 7.46 (m, 1H), 7.37-7.26 (m, 6H), 7.22-7.19 (m, 1H), 7.07 (s, 1H), 6.85-6.82 (m, 1H), 5.25 (s, 2H), 4.39 (s, 2H), 3.54 (t, J=6.3 Hz, 2H), 2.88 (t, J=6.3 Hz, 2H).

Sources & evidence

ORD record: ord-7ce6e939e6924911b2ec22fc13f66ea4
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07579470B2

Reaction notes

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