Benzylamine → 1-Benzyl-3-(3-chloro-4-fluoro-phenyl)-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine

HRID 749693Notes

Reaction equation

HRID 749693 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)=O)(C)(C)C.[CH2:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[Cl:23][C:24]1[CH:29]=[C:28]([CH:30]=[CH:31][N+]([O-])=O)[CH:27]=[CH:26][C:25]=1[F:35]>>[CH2:15]([N:22]1[C:11]2[CH2:10][CH2:9][NH:8][CH2:13][C:12]=2[C:30]([C:28]2[CH:27]=[CH:26][C:25]([F:35])=[C:24]([Cl:23])[CH:29]=2)=[CH:31]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 3

HCID 7504BenzylamineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 668018422-Chloro-1-fluoro-4-(2-nitro-vinyl)-benzene

Product 1

HCID 114050911-Benzyl-3-(3-chloro-4-fluoro-phenyl)-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine

Procedure

The title compound (0.18 g) was prepared from 0.54 g of 4-oxo-piperidine-1-carboxylic acid tert-butyl ester, 293 μL of benzylamine, and 0.62 g of 2-chloro-1-fluoro-4-(2-nitro-vinyl)-benzene. MS (ESI): exact mass calculated for C20H18ClFN2, 340.11; found, m/z 341.1 [M+H]+, 343.2 [M+H]+. 1H NMR (500 MHz, CD3OD): 7.45-7.43 (m, 1H), 7.36-7.16 (m, 8H), 5.15 (s, 2H), 4.35 (s, 2H), 3.50 (t, J=6.3 Hz, 2H), 2.85 (t, J=6.3 Hz, 2H).

Sources & evidence

ORD record
ord-f45119a411e548d4bcbbcd7b5a5bb963
Source dataset
uspto-grants-2008_07
Patent number
US07402680B2

Reaction notes

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