Hydrochloric Acid → HCID 9924104, compound

HRID 1005660Notes

Reaction equation

HRID 1005660 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[NH:19][CH:18]=[C:17]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.Cl.[OH-].[NH4+]>C(O)C.O>[C:26]1([S:23]([C:17]2[C:16]3[C:20](=[CH:21][CH:22]=[C:14]([N:11]4[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]4)[CH:15]=3)[NH:19][CH:18]=2)(=[O:24])=[O:25])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 60108784HCID 60108784, compound

Product 1

HCID 9924104HCID 9924104, compoundYield 95.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

4-(3-Benzenesulfonyl-1H-indol-5-yl)-piperazine-1-carboxylic acid tert-butyl ester (0.5 g, 1.13 mmol) was dissolved in 5 mL of ethanol and 3 mL of conc. hydrochloric acid were added. The mixture was heated to a gentle boil for 2-3 min, cooled to room temperature, basified with ammonium hydroxide, and diluted with 20 mL of water. After the mixture was allowed to stand overnight, the solid was filtered, washed with water and dried to give 0.37 g of 3-benzenesulfonyl-5-piperazin-1-yl-1H-indole (201) as a tan crystalline solid, m.p. 254-264° C. (dec).

Workup

  1. temperatureThe mixture was heated to a gentle boil for 2-3 min
  2. filtrationthe solid was filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-8531c574d6cb47a797c9ea52babe1f02
Source dataset
uspto-grants-2004_09
Patent number
US06787535B2

Reaction notes

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