Hydrochloric Acid → 2-(4-Aminophenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochloride

HRID 2036720Notes

Reaction equation

HRID 2036720 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[N:16]([CH3:20])[C:15]2[CH2:21][CH:22]4[NH:26][CH:25]([C:14]3=2)[CH2:24][CH2:23]4)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[ClH:27]>CO>[ClH:27].[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[N:16]([CH3:20])[C:15]2[CH2:21][CH:22]4[NH:26][CH:25]([C:14]3=2)[CH2:24][CH2:23]4)(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 582588562-(4-Aminophenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole

Product 1

HCID 670855212-(4-Aminophenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the product of step C (25 mg, 0.06 mmol) was added 1.25 M HCl in methanol (1 mL). The solution was concentrated in vacuo and the residue triturated with ethyl acetate before it was lyophilized from water to give 2-(4-aminophenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochloride (15 mg, 62%, AUC HPLC 98.3%) as a white solid: mp 220-225° C.; 1H NMR (CD3OD, 300 MHz) δ 8.21 (s, 1H), 7.78 (d, J=7.8 Hz, 1H), 7.75 (s, 2H), 7.66-7.70 (m, 1H), 7.55 (d, J=9.0 Hz, 1H), 6.96 (d, J=8.1 Hz, 1H), 5.28 (d, J=4.8 Hz, 1H), 4.54 (br s, 1H), 3.72 (s, 3H), 3.44-3.53 (m, 1H), 3.03-3.07 (m, 1H), 2.24-2.47 (m, 3H), 1.95-2.01 (m, 1H); ESI MS m/z 368 [M+H]+.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customthe residue triturated with ethyl acetate before it

Sources & evidence

ORD record
ord-49218c7719f7405aa34fce17fe7472e4
Source dataset
uspto-grants-2013_11
Patent number
US08575186B2

Reaction notes

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