Hydrochloric Acid → 5-chloro-2-(piperazine-1-sulfonyl)-1H-indole

HRID 353458Notes

Reaction equation

HRID 353458 reaction equation
C1(S([N:10]2[C:18]3[C:13](=[CH:14][C:15]([Cl:19])=[CH:16][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:15]1[CH:14]=[C:13]2[C:18](=[CH:17][CH:16]=1)[NH:10][C:11]([S:20]([N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)(=[O:22])=[O:21])=[CH:12]2

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 235137361-(1-Benzenesulphonyl-5-chloroindol-2-ylsulphonyl)piperazine

Product 1

HCID 227105715-chloro-2-(piperazine-1-sulfonyl)-1H-indole

Conditions

Temperature
80 °C

Procedure

The requisite 1-(5-chloroindol-2-ylsulphonyl)piperazine starting material was prepared as follows 1-(1-Benzenesulphonyl-5-chloroindol-2-ylsulphonyl)piperazine (4.15 g, 9.44 mmol) was treated with sodium hydroxide solution (32 ml of 2.5M), giving a yellow suspension. This was warmed to 80° C. with vigorous stirring and stirred for 45 mins, giving complete solution. The solution 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-(5-chloroindol-2-ylsulphonyl)piperazine as a pale yellow solid, 1H NMR (d6DMSO) 2.75 ppm (m, 4H), 2.9 ppm (m, 4H), 7.0 ppm (s, 1H), 7.3 ppm (dd, 1H), 7.5 ppm (d, 1H), 7.8 ppm (d, 1H); MS (M+H)+ 300/302.

Workup

  1. customThe requisite 1-(5-chloroindol-2-ylsulphonyl)piperazine starting material was prepared
  2. customgiving a yellow suspension
  3. stirringstirred for 45 mins
  4. customgiving complete solution
  5. temperatureThe solution was cooled to ambient temperature
  6. filtrationthe resultant precipitate was filtered off
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-f53154b25cc848269a93030dd016e924
Source dataset
uspto-grants-2004_06
Patent number
US06753331B1

Reaction notes

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