Hydrochloric Acid → 4-Piperidinamine, 1-(1-phenylcyclohexyl)-

HRID 1588223Notes

Reaction equation

HRID 1588223 reaction equation
[C:1]1([C:7]2([N:13]3[CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]3)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:26].[Na+].Cl.C(=O)([O-])[O-].[K+].[K+]>CO.O>[NH2:26][CH:16]1[CH2:17][CH2:18][N:13]([C:7]2([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH2:14][CH2:15]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 4250911-(1-Phenylcyclohexyl)piperidin-4-oneHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 110543604-Piperidinamine, 1-(1-phenylcyclohexyl)-

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

1-(1-Phenylcyclohexyl)-4-piperidone (0.245 g) and ammonium acetate (1 g) were dissolved in 3.5 ml dry methanol. After stirring at room temperature for 10 minutes, sodium cyanoborohydride (0.1 g) was added and the reaction stoppered. After 20 hours, 0.1 ml concentrated hydrochloric acid was added followed by 10 ml water and the mixture was stirred for 1.5 hours. The solution was basified with potassium carbonate to pH 9 and extracted with methylene chloride. The methylene chloride was dried over Na2SO4 and removed in vacuo. The product distilled as a colorless, clear oil at 90°-130° C. in vacuo (about 5 mmHg).

Workup

  1. waitAfter 20 hours
  2. stirringthe mixture was stirred for 1.5 hours
  3. extractionextracted with methylene chloride
  4. dry with materialThe methylene chloride was dried over Na2SO4
  5. customremoved in vacuo
  6. distillationThe product distilled as a colorless, clear oil at 90°-130° C. in vacuo (about 5 mmHg)

Sources & evidence

ORD record
ord-41e8c88c76dc42d184ec29f53c2ce388
Source dataset
uspto-grants-1993_06
Patent number
US05221629

Reaction notes

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