Hydrochloric Acid → 10-(2-Fluorophenyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole hydrochloride

HRID 1370363Notes

Reaction equation

HRID 1370363 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][C:23]=4[F:28])=[CH:16][CH:15]=[CH:14][C:13]=3[NH:12][C:11]=2[CH2:10][CH2:9]1)C1C=CC=CC=1.[ClH:29]>C(O)C.[Pd]>[ClH:29].[F:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[C:17]1[C:18]2[C:19]3[CH2:20][CH2:21][NH:8][CH2:9][CH2:10][C:11]=3[NH:12][C:13]=2[CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 223967213-Benzyl-10-(2-fluorophenyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole

Product 1

HCID 2239669910-(2-Fluorophenyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole hydrochlorideYield 17.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-benzyl-10-(2-fluorophenyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (0.11 g, 0.30 mmol), 1 N hydrochloric acid (0.3 mL, 0.3 mmol) and Pd/C (10%, 0.2 g) in ethanol (50.0 mL) was reacted in a manner similar to Example 8 to give 0.017 g of the title compound as a pale green solid: mp>259° C. (dec.); 1H NMR (300 MHz, DMSO-d6) δ 11.29, 9.29, 7.51-7.41, 7.39-7.25, 7.08, 6.77, 3.33-3.20, 3.20-3.09, 3.09-2.99, 2.63-2.50; MS (EI) m/z 294 (M+).

Workup

  1. customwas reacted in a manner similar to Example 8

Sources & evidence

ORD record
ord-28ce9c38509c40489af6c71264531a67
Source dataset
uspto-grants-2003_06
Patent number
US06583135B2

Reaction notes

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