Hydrochloric Acid → HCID 22396910, compound

HRID 1356233Notes

Reaction equation

HRID 1356233 reaction equation
C([N:8]1[CH2:21][CH2:20][C:19]2[C:18]3[CH:17]=[C:16]([C:22]4[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=4)[CH:15]=[CH:14][C:13]=3[NH:12][C:11]=2[CH2:10][CH2:9]1)C1C=CC=CC=1.[ClH:30]>C(O)C.[Pd]>[ClH:30].[CH3:29][O:28][C:25]1[CH:26]=[CH:27][C:22]([C:16]2[CH:15]=[CH:14][C:13]3[NH:12][C:11]4[CH2:10][CH2:9][NH:8][CH2:21][CH2:20][C:19]=4[C:18]=3[CH:17]=2)=[CH:23][CH:24]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 10339881HCID 10339881, compound

Product 1

HCID 22396910HCID 22396910, compoundYield 82.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-benzyl-9-(4-methoxyphenyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (0.22 g, 0.62 mmol), 1 N hydrochloric acid (0.65 mL, 0.65 mmol) and Pd/C (10%, 0.24 g) in ethanol (50.0 mL) was reacted in a manner similar to Example 8 to give 0.168 g (80%) of a greenish solid: mp 258-5 260° C.; 1H NMR (400 MHz, DMSO-d6) δ 11.08, 9.62, 7.64, 7.59, 7.31, 6.99, 3.79, 3.37-3.27, 3.22-3.12; IR (drift) 2986, 2957, 2921, 2893, 2829, 2752, 1514, 1476, 1456, 1273, 1250, 1239, 1180, 836, 800 cm−1; MS (EI) m/z 292 (M+); HRMS (FAB) calcd for C19H20N2O+H: 293.1654, found: 293.1651; Anal. Calcd for C19H20N2O.HCl: C, 69.40; H, 6.44; N, 8.52; Found: C, 68.37; H, 6.53; N, 8.27.

Workup

  1. customwas reacted in a manner similar to Example 8

Sources & evidence

ORD record
ord-b5f14620c31747819a0291ff8c734368
Source dataset
uspto-grants-2003_07
Patent number
US06586421B2

Reaction notes

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