1-(2-Chlorophenyl)piperidine-4-carboxamide → 1-[1-(2-Chlorophenyl)piperid-4-yl]methylamine

HRID 964008Notes

Reaction equation

HRID 964008 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:13][CH2:12][CH:11]([C:14]([NH2:16])=O)[CH2:10][CH2:9]1.B.CSC>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:9][CH2:10][CH:11]([CH2:14][NH2:16])[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 105141271-(2-Chlorophenyl)piperidine-4-carboxamideHCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 107755461-[1-(2-Chlorophenyl)piperid-4-yl]methylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(2-chlorophenyl)piperidine-4-carboxamide (0.25 g, prepared in a similar manner to that described above) was dissolved in tetrahydrofuran (25 ml) and borane-dimethyl sulphide complex (1M in dimethyl sulphide; 0.4 ml) was added. The resulting solution was heated under reflux for 2 hours. The solvent was removed in vacuo, hydrochloric acid (1M; 50 ml) was added, and the mixture stirred at ambient temperature for 1 hour. The solution was basified by the addition of aqueous sodium hydroxide solution (5M) and the product extracted into ether. The extracts were washed with water then dried over magnesium sulphate and the solvent removed in vacuo to give 1-[1-(2-chlorophenyl)piperid-4-yl]methylamine as an oil (0.19 g). The reaction was repeated on a 4.4× scale to give further 1-[1-(2-chlorophenyl)piperid-4-yl]methylamine (1.0 g).

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureunder reflux for 2 hours
  3. customThe solvent was removed in vacuo, hydrochloric acid (1M; 50 ml)
  4. additionwas added
  5. additionThe solution was basified by the addition of aqueous sodium hydroxide solution (5M)
  6. extractionthe product extracted into ether
  7. washThe extracts were washed with water
  8. dry with materialthen dried over magnesium sulphate
  9. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-a71d8aab9cd542a0b11276cc5db00e06
Source dataset
uspto-grants-1998_06
Patent number
US05767116

Reaction notes

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