Water → HCID 12608504, compound

HRID 460784Notes

Reaction equation

HRID 460784 reaction equation
[S-:1][C:2]#[N:3].[NH4+].[C:5](Cl)(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[NH2:14][CH:15]1[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][C:23]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[NH:25][CH:24]=2)[CH2:17][CH2:16]1.O>CC(C)=O>[C:5]([NH:3][C:2]([NH:14][CH:15]1[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][C:23]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[NH:25][CH:24]=2)[CH2:17][CH2:16]1)=[S:1])(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 15666Ammonium thiocyanateHCID 2154154-Piperidinamine, 1-(2-(1H-indol-3-yl)ethyl)-, hydrate

Product 1

HCID 12608504HCID 12608504, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent3×

Procedure

To a stirred solution of ammonium thiocyanate (2.28g) in dry acetone (20 ml) was added a solution of benzoyl chloride (4.22g) in dry acetone (20 ml). This mixture was stirred at 45° for 5 min. then treated with a solution of 3-[2-(4-aminopiperidyl)-ethyl]indole (7.84g) in dry acetone (30 ml). After refluxing for 25 min, the mixture was cooled, poured into water (250 ml) and the liberated oil extracted into chloroform. Evaporation of the dried (MgSO4) extract afforded the title compound which was crystallised from EtOH-HCl/Et2O as the hydrochloride (1.65 g), m.p. 212°-215°.

Workup

  1. temperatureAfter refluxing for 25 min
  2. temperaturethe mixture was cooled
  3. extractionthe liberated oil extracted into chloroform
  4. customEvaporation of the
  5. dry with materialdried (MgSO4)
  6. extractionextract

Sources & evidence

ORD record
ord-d664b7bda91842ccafe5200ea0d79bf7
Source dataset
uspto-grants-1977_12
Patent number
US04061641

Reaction notes

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