3-Benzyl-10-phenyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole → 10-Phenyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole

HRID 1370362Notes

Reaction equation

HRID 1370362 reaction equation
C([N:8]1[CH2:21][CH2:20][C:19]2[C:18]3[C:17]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:16][CH:15]=[CH:14][C:13]=3[NH:12][C:11]=2[CH2:10][CH2:9]1)C1C=CC=CC=1>C(O)(=O)C.C(O)C.[Pd]>[C:22]1([C:17]2[C:18]3[C:19]4[CH2:20][CH2:21][NH:8][CH2:9][CH2:10][C:11]=4[NH:12][C:13]=3[CH:14]=[CH:15][CH:16]=2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 1

HCID 223967273-Benzyl-10-phenyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole

Product 1

HCID 2239680710-Phenyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indoleYield 121.7%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-benzyl-10-phenyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (0.22 g, 0.62 mmol), glacial acetic acid (2 drops) and Pd/C (10%, 0.11 g) in ethanol (50.0 mL) was reacted in a manner similar to Example 8 to give 0.198 g (90%) of a brown foam. Crystallization from ethyl acetate gave 0.030 g of the title compound as a beige solid: mp>250° C.; 1H NMR (300 MHz, CDCl3) δ 7.97, 7.48-7.36, 7.16, 6.94, 3.12-3.08, 3.02-2.98, 2.87-2.83, 2.47-2.43; IR (drift) 3053, 3025, 2927, 2895, 2833, 1458, 1428, 1415, 1335, 1292, 1262, 790, 760, 751, 703 cm−1; MS (EI) m/z 262 (M+); HRMS (FAB) calcd for C18H18N2+H: 263.1548, found 263.1550.

Workup

  1. customwas reacted in a manner similar to Example 8

Sources & evidence

ORD record
ord-7f567dbbd4d140ce89470d82ced63cb8
Source dataset
uspto-grants-2003_06
Patent number
US06583135B2

Reaction notes

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