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

HRID 749729

Reaction equation

HRID 749729 reaction equation
C(O[C:4]([N:6]1[CH2:11][CH2:10][C:9](=O)[CH2:8][CH2:7]1)=O)C.[CH2:13]([NH2:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Cl:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH:28]=[CH:29][N+]([O-])=O)[CH:23]=1.N>CO.CCOC(C)=O>[CH2:13]([N:20]1[C:9]2[CH2:8][CH2:7][N:6]([CH3:4])[CH2:11][C:10]=2[C:28]([C:24]2[CH:25]=[CH:26][CH:27]=[C:22]([Cl:21])[CH:23]=2)=[CH:29]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 7504BenzylamineHCID 34767Ethyl 4-oxo-1-piperidinecarboxylateHCID 27316461-Chloro-3-(2-nitroethenyl)benzene

Product 1

HCID 597525111-Benzyl-3-(3-chloro-phenyl)-5-methyl-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Procedure

The title compound (0.34 g) was prepared from 3.0 g of 4-oxo-piperidine-1-carboxylic acid ethyl ester, 1.91 mL of benzylamine, and 1.2 g of 1-chloro-3-(2-nitro-vinyl)-benzene as in Example 38. TLC (SiO2, 2% NH3 in MeOH/EtOAc): Rf=0.25. MS (ESI): exact mass calculated for C21H21ClN2, 336.14; found, m/z 337.2 [M+H]+, 339.2 [M+H]+. 1H NMR (500 MHz, CD3OD): 7.36-7.32 (m, 4H), 7.30-7.25 (m, 2H), 7.21-7.16 (m, 4H), 5.15 (s, 2H), 4.41 (s, 2H), 3.53 (t, J=6.3 Hz, 2H), 2.98 (s, 3H), 2.91 (t, J=6.3 Hz, 2H), 2.82-2.70 (m, 4H).

Sources & evidence

ORD record
ord-8818a301c88c423e9ac69a81921c7f6e
Source dataset
uspto-grants-2008_07
Patent number
US07402680B2

Linked notes

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