2-Fluorobenzylamine → HCID 59752543, compound

HRID 599873Notes

Reaction equation

HRID 599873 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)=O)(C)(C)C.[F: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][C:32]([Cl:35])=[CH:31][CH:30]=1)([O-])=O>>[Cl:35][C:32]1[CH:33]=[CH:34][C:29]([C:28]2[C:12]3[CH2:13][NH:8][CH2:9][CH2:10][C:11]=3[N:19]([CH2:18][C:17]3[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=3[F:15])[CH:27]=2)=[CH:30][CH:31]=1

Participants

4

Reactant 3

HCID 666492-FluorobenzylamineHCID 95339p-Chloro-beta-nitrostyreneHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 59752543HCID 59752543, compound

Procedure

The title compound (129.2 mg) was prepared from 0.49 g of 4-oxo-piperidine-1-carboxylic acid tert-butyl ester, 286 μL of 2-fluorobenzylamine, and 0.46 g of (2-nitro-vinyl)-4-chlorobenzene, replacing SiO2 with crushed 4 Å molecular sieves. MS (ESI): exact mass calculated for C20H18ClFN2, 340.11. found, m/z 341.1 [M+H]+. 1H NMR (500 MHz, CD3OD): 7.38-7.30 (m, 5H), 7.18-7.12 (m, 3H), 7.10-7.06 (m, 1H), 5.20 (s, 2H), 4.35-4.34 (m, 2H), 3.54 (t, J=6.3 Hz, 2H), 2.94 (t, J=6.3 Hz, 2H).

Workup

  1. customwith crushed 4 Å molecular sieves

Sources & evidence

ORD record
ord-e0ba6c9dff41468eba5bb0e858368bb9
Source dataset
uspto-grants-2011_03
Patent number
US07897771B2

Reaction notes

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