Hydrochloric Acid → HCID 23513739, compound

HRID 353461Notes

Reaction equation

HRID 353461 reaction equation
C1(S([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([Cl:19])[CH:17]=3)[CH:12]=[C:11]2[S:20]([N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)(=[O:22])=[O:21])(=O)=O)C=CC=CC=1.[OH-].[Na+].Cl>>[Cl:19][C:16]1[CH:17]=[C:18]2[C:13]([CH:12]=[C:11]([S:20]([N:23]3[CH2:24][CH2:25][NH:26][CH2:27][CH2:28]3)(=[O:21])=[O:22])[NH:10]2)=[CH:14][CH:15]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23513735HCID 23513735, compound

Product 1

HCID 23513739HCID 23513739, compound

Procedure

The requisite 1-(6-chloroindol-2-ylsulphonyl)piperazine starting material was prepared as follows. 1-(1-Benzenesulphonyl-6-chloroindol-2-ylsulphonyl)piperazine (500 mg, 1.18 mmol) was treated with sodium hydroxide solution (4 ml of 10M), and the suspension refluxed for 2 hrs. The reaction mixture was cooled to ambient temperature and carefully treated with concentrated hydrochloric acid to pH 8; the resultant precipitate was filtered off, washed with water and dried to give 1-(6-chloroindol-2-ylsulphonyl)piperazine as a pale yellow solid which was used without further purification; 1H NMR (d6DMSO) 3.1 ppm (m, 4H), 3.2 ppm (m, 4H), 7.1 ppm (s, 1H), 7.2 ppm (dd, 1H), 7.5 ppm (s, 1H), 7.7 ppm (d, 1H); the spectrum also contained signals due to benzene sulphonic acid (ca 25 mol %); MS (M+H)+ 300/302.

Workup

  1. customThe requisite 1-(6-chloroindol-2-ylsulphonyl)piperazine starting material was prepared
  2. temperaturethe suspension refluxed for 2 hrs
  3. filtrationthe resultant precipitate was filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-2d094b64d82041a3ae3eebdaec0153b6
Source dataset
uspto-grants-2004_06
Patent number
US06753331B1

Reaction notes

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