Water → HCID 20333079, compound

HRID 1706927Notes

Reaction equation

HRID 1706927 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S-:10][C:11]#[N:12].[NH4+].[NH2:14][CH:15]1[CH2:20][CH2:19][N:18]([CH2:21][C:22]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[NH:24][CH:23]=2)[CH2:17][CH2:16]1.O>CC(C)=O>[NH:24]1[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:22]([CH2:21][N:18]2[CH2:19][CH2:20][CH:15]([NH:14][C:11]([NH:12][C:1](=[O:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[S:10])[CH2:16][CH2:17]2)=[CH:23]1

Participants

6

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 15666Ammonium thiocyanateHCID 111722501-(1H-indol-3-ylmethyl)piperidin-4-amine

Product 1

HCID 20333079HCID 20333079, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Benzoyl chloride (0.49 g, 3.5 mmol) was added to a solution of ammonium thiocyanate (0.29 g, 3.82 mmol) in dry acetone (4 cm3). The reaction mixture was heated under reflux for 10 minutes, then 4-amino-1-(indol-3-ylmethyl)piperidine (0.78 g, 3.41 mmol) was added. The suspension was stirred at room temperature for 1 hour then heated under reflux for 15 minutes and poured into water (20 cm3), precipitating an oil. The supernatant aqueous phase was decanted and the oil triturated with propan-2-ol under reflux to give the title compound as the hydrocyanate salt (0.18 g, 11.7%), m.p. 183°-185° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 10 minutes
  3. temperaturethen heated
  4. temperatureunder reflux for 15 minutes
  5. customprecipitating an oil
  6. customThe supernatant aqueous phase was decanted
  7. customthe oil triturated with propan-2-ol
  8. temperatureunder reflux

Sources & evidence

ORD record
ord-b882a30c169441089379e7b28187a152
Source dataset
uspto-grants-1980_06
Patent number
US04209521

Reaction notes

Loading…