Water → tert-Butyl 4-((methylamino)methyl)piperidine-1-carboxylate

HRID 1978344Notes

Reaction equation

HRID 1978344 reaction equation
[CH3:1][N:2]([CH2:9][CH:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]1)C(=O)C(F)(F)F.[BH4-].[Na+].O.C(Cl)Cl>C(O)C>[CH3:1][NH:2][CH2:9][CH:10]1[CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14][CH2:15]1

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 4311764Sodium borohydride2×HCID 21994204N-methyl-N-(1-tert-butoxycarbonylpiperidin-4-ylmethyl)trifluoroacetamide

Product 1

HCID 21934652tert-Butyl 4-((methylamino)methyl)piperidine-1-carboxylateYield 107.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1.32 g (4.07 mM) of N-methyl-N-(1-tert-butoxycarbonylpiperidin-4-ylmethyl)trifluoroacetamide in ethanol was added 0.23 g (6.08 mM) of sodium borohydride at room temperature and the mixture was stirred at room temperature for 2.5 hours. To this reaction mixture was further added 0.27 g (7.1 mM) of sodium borohydride and the mixture was stirred at room temperature for 20 hours. The mixture was then stirred at 60° C. for 1.5 hours. To this reaction mixture was added water to stop the reaction and methylene chloride was added for extraction. The organic layer was washed with saturated aqueous solution of sodium chloride and dried over MgSO4. The solvent was then distilled off to provide the title compound as colorless oil (1.00 g, quantitative).

Workup

  1. stirringthe mixture was stirred at room temperature for 20 hours
  2. stirringThe mixture was then stirred at 60° C. for 1.5 hours
  3. additionwas added for extraction
  4. washThe organic layer was washed with saturated aqueous solution of sodium chloride
  5. dry with materialdried over MgSO4
  6. distillationThe solvent was then distilled off

Sources & evidence

ORD record
ord-ce01fee7eda348f1b171d25839f426bd
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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