Hydrochloric Acid → 2-Phenyl-1-(phenylsulfonyl)-4-(1-piperazinyl)-1H-indole Hydrochloride

HRID 8342

Reaction equation

HRID 8342 reaction equation
[C:1]1([C:7]2[N:8]([S:29]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)(=[O:31])=[O:30])[C:9]3[C:14]([CH:15]=2)=[C:13]([N:16]2[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]2)[CH:12]=[CH:11][CH:10]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:38]>C(Cl)Cl.CCOCC>[ClH:38].[C:1]1([C:7]2[N:8]([S:29]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)(=[O:30])=[O:31])[C:9]3[C:14]([CH:15]=2)=[C:13]([N:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[CH:12]=[CH:11][CH:10]=3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 22015379tert-Butyl 4-[2-phenyl-1-(phenylsulfonyl)-1H-indol-4-yl]-1-piperazinecarboxylate

Product 1

HCID 102759432-Phenyl-1-(phenylsulfonyl)-4-(1-piperazinyl)-1H-indole Hydrochloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-[2-phenyl-1-(phenylsulfonyl)-1H-indol-4-yl]-1-piperazinecarboxylate (30 mg, 0.058 mmol) was dissolved in CH2Cl2 (1 mL) followed by addition of HCl in ether (1 mL). The reaction was shaken for 2 h at room temperature. The resulting precipitate was filtered off and washed with ether giving 20 mg of the desired compound (80%). 1H NMR (270 MHz, DMSO-d6) δ 9.02 (br, 1 H), 7.90–7.80 (m, 3 H), 7.75–7.55 (m, 3 H), 7.32 (s, 1 H), 7.22 (t, J=8 Hz, 1 H), 6.79 (d, J=8 Hz, 1 H), 3.35–310 (m, 8 H). MS (ESI+) for m/z 418 (M+H)+.

Workup

  1. filtrationThe resulting precipitate was filtered off
  2. washwashed with ether giving 20 mg of the desired compound (80%)

Sources & evidence

ORD record
ord-0935eb894ecc468c996ee9c9067d7403
Source dataset
uspto-grants-2006_08
Patent number
US07087750B2

Linked notes

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