Sodium Chloride → 4-Amino-1-Boc-piperidine

HRID 1978311Notes

Reaction equation

HRID 1978311 reaction equation
FC(F)(F)C([NH:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)=O.C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])O.[Na+].[Cl-].[Na+]>CO>[NH2:5][CH:6]1[CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:10][CH2:11]1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 21993671HCID 21993671, compound

Product 1

HCID 12682914-Amino-1-Boc-piperidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 7.35 g (24.8 mM) of tert-butyl 4-trifluoroacetamido-1-piperidinecarboxylate and 5.71 g (41.3 mM) of potassium carbonate in 50 ml of methanol was stirred at 60° C. for 8 hours. This reaction mixture was poured in aqueous solution of sodium hydrogen carbonate and the mixture was saturated with sodium chloride and extracted with 10 portions of ethyl acetate. The pooled organic layer was dried over MgSO4 and the solvent was distilled off under reduced pressure to recover the title compound as light-yellow liquid. This crude product was not purified but used as it was in the next reaction.

Workup

  1. extractionextracted with 10 portions of ethyl acetate
  2. dry with materialThe pooled organic layer was dried over MgSO4
  3. distillationthe solvent was distilled off under reduced pressure
  4. customto recover the title compound as light-yellow liquid
  5. customThis crude product was not purified
  6. customwas in the next reaction

Sources & evidence

ORD record
ord-db33101a23044ef0975f3ad7636921ff
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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