Hydrochloric Acid → 4-[(3-Phenylpropan-1-yl)aminomethyl]-piperidine

HRID 1978350Notes

Reaction equation

HRID 1978350 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][N:10]([CH2:17][CH:18]2[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]2)C(=O)C(F)(F)F)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[OH-].[Na+]>C(O)C>[C:1]1([CH2:7][CH2:8][CH2:9][NH:10][CH2:17][CH:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21993736N-(3-phenylpropan-1-yl)-N-[1-tert-butoxycarbonylpiperidin-4-ylmethyl]trifluoroacetamide

Product 1

HCID 219936474-[(3-Phenylpropan-1-yl)aminomethyl]-piperidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 1.49 g (3.48 mM) of N-(3-phenylpropan-1-yl)-N-[1-tert-butoxycarbonylpiperidin-4-ylmethyl]trifluoroacetamide in ethanol (10 ml) was added 1.0 ml (12 mM) of 12N-hydrochloric acid at room temperature and the mixture was stirred for 20 hours. The solvent was then distilled off under reduced pressure and 3 ml (36 mM) of 12N-hydrochloric acid was added to the residue. This mixture was stirred at room temperature for 20 minutes. To this reaction mixture was added ethanol and the solvent was distilled off under reduced pressure to provide 1.29 g (quantitative) of a crude product as white solid. To a solution of 0.33 g (0.90 mM) of this crude product in ethanol (4 ml) was added 4 ml (4 mM) of 1N-aqueous solution of sodium hydroxide at room temperature and the mixture was stirred for 30 minutes. The ethanol was then distilled off under reduced pressure and the residue was extracted with chloroform. The organic layer was washed with saturated aqueous solution of sodium chloride and dried over MgSO4. The solvent was then distilled off under reduced pressure to provide the title compound.

Workup

  1. distillationThe solvent was then distilled off under reduced pressure and 3 ml (36 mM) of 12N-hydrochloric acid
  2. additionwas added to the residue
  3. stirringThis mixture was stirred at room temperature for 20 minutes
  4. additionTo this reaction mixture was added ethanol
  5. distillationthe solvent was distilled off under reduced pressure
  6. customto provide 1.29 g (quantitative) of a crude product as white solid
  7. stirringthe mixture was stirred for 30 minutes
  8. distillationThe ethanol was then distilled off under reduced pressure
  9. extractionthe residue was extracted with chloroform
  10. washThe organic layer was washed with saturated aqueous solution of sodium chloride
  11. dry with materialdried over MgSO4
  12. distillationThe solvent was then distilled off under reduced pressure

Sources & evidence

ORD record
ord-060f9d9a5f9347188361bfaa124087b9
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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