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

HRID 1654445Notes

Reaction equation

HRID 1654445 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 was stoppered. After 20 hours, 0.1 mL of 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-4df8efb526da402ba229fa2e06c19e4e
Source dataset
uspto-grants-1995_04
Patent number
US05407834

Reaction notes

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