HCID 10020923, compound → HCID 22397017, compound

HRID 1370360Notes

Reaction equation

HRID 1370360 reaction equation
C([N:8]1[CH2:21][CH2:20][C:19]2[C:18]3[CH:17]=[CH:16][C:15]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[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:15]2[CH:16]=[CH:17][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]=2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 1

HCID 10020923HCID 10020923, compound

Product 1

HCID 22397017HCID 22397017, compoundYield 51%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-benzyl-8-phenyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (1.07 g, 3.0 mmol), glacial acetic acid (2 drops) and Pd/C (10%, 0.6 g) in ethanol (150 mL) was reacted in a manner similar to Example 8 to give 0.40 g (51%) of the title compound as a tan crystalline solid: mp 220-222° C.; 1H NMR (400 MHz, DMSO-d6) δ 10.41, 7.61-7.59, 7.46, 7.42-7.38, 7.28-7.22, 3.04-3.01, 2.96-2.94, 2.87-2.84; 13C NMR (100 MHz, DMSO-d6) δ 142.4, 138.2, 135.3, 133.0, 128.5, 128.4, 126.8, 126.0, 117.9, 117.5, 111.8, 108.8, 50.5, 48.8, 32.5, 28.0; IR (drift) 3305, 2929, 2918, 2893, 2827, 1468, 1324, 1242, 869, 814, 787, 762, 753, 743, 700 cm−1; MS (EI) m/z 262 (M+); HRMS (FAB) calcd for C18H18N2+H: 263.1548, found: 263.1543; Anal. Calcd for C18H18N2.0.1C2H4O2; C, 81.46; H, 6.91; N, 10.44. Found: C, 81.11; H, 7.01; N, 10.35.

Workup

  1. customwas reacted in a manner similar to Example 8

Sources & evidence

ORD record
ord-b278d507bc6a4493b8b18d65f311495d
Source dataset
uspto-grants-2003_06
Patent number
US06583135B2

Reaction notes

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