Dichloromethane → HCID 69351600, compound

HRID 1005659Notes

Reaction equation

HRID 1005659 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[CH:16][CH:17]=[C:18]3[C:22]=2[NH:21][CH:20]=[C:19]3[S:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)(=[O:25])=[O:24])[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.[Cl:39]CCl>>[ClH:39].[C:26]1([S:23]([C:19]2[C:18]3[C:22](=[C:14]([N:11]4[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]4)[CH:15]=[CH:16][CH:17]=3)[NH:21][CH:20]=2)(=[O:24])=[O:25])[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 60108791HCID 60108791, compound

Product 1

HCID 69351600HCID 69351600, compound

Procedure

4-(3-Benzenesulfonyl-1H-indol-7-yl)-piperazine-1-carboxylic acid tert-butyl ester (1 g, 2.2 mmol) was dissolved in 5 mL of dichloromethane and 6 mL of trifluoroacetic acid was added. After 10 min the mixture was concentrated in vacuo, taken into water, and washed with ether. The aqueous layer was basified with ammonium hydroxide, extracted with dichloromethane, and the extract was dried (sodium sulfate) and evaporated to afford the crude free base. The hydrochloride salt was crystallized from ethanol to afford 550 mg of 3-benzenesulfonyl-7-piperazin-1-yl-1H-indole hydrochloride (101), m.p. 278-280° C.

Workup

  1. concentrationAfter 10 min the mixture was concentrated in vacuo
  2. washwashed with ether
  3. extractionextracted with dichloromethane
  4. dry with materialthe extract was dried (sodium sulfate)
  5. customevaporated
  6. customto afford the crude free base
  7. customThe hydrochloride salt was crystallized from ethanol

Sources & evidence

ORD record
ord-5950f714b95e44fa824208c5b0834406
Source dataset
uspto-grants-2004_09
Patent number
US06787535B2

Reaction notes

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