Hydrochloric Acid → HCID 22396744, compound

HRID 1356236Notes

Reaction equation

HRID 1356236 reaction equation
C([N:8]1[CH2:21][CH2:20][C:19]2[C:18]3[C:17]([C:22]4[CH:27]=[C:26]([F:28])[CH:25]=[C:24]([F:29])[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.[ClH:30]>C(O)C.[Pd]>[ClH:30].[F:29][C:24]1[CH:23]=[C:22]([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:27]=[C:26]([F:28])[CH:25]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 22396587HCID 22396587, compound

Product 1

HCID 22396744HCID 22396744, compoundYield 46.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-benzyl-10-(3,5-difluorophenyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (0.35 g, 0.90 mmol), 1 N hydrochloric acid (0.9 mL, 0.9 mmol) and Pd/C (10%, 0.5 g) in ethanol (50 mL) was reacted in a manner similar to Example 8 to give 0.14 g of the title compound as a cream-colored solid: m p>267° C. (dec.); 1H NMR (400 MHz, DMSO-d6) δ 11.42, 9.57, 7.37, 7.30-7.25, 7.11-7.07, 6.84, 6.78-6.76, 3.35-3.27, 3.25-3.18, 3.16-3.08, 2.63-2.56; IR (drift) 3259, 2956, 2861, 2811, 2778, 2699, 2641, 2455, 1622, 1591, 1458, 1332, 1113, 985, 749 cm−1; HRMS (FAB) calcd for C18H16F2N2+H: 299.1360, found: 299.1369.

Workup

  1. customwas reacted in a manner similar to Example 8

Sources & evidence

ORD record
ord-a6c976686bff4459a15d1538f4855cab
Source dataset
uspto-grants-2003_07
Patent number
US06586421B2

Reaction notes

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