Sodium Methoxide → 2-Piperidinone, 3-amino-3-(difluoromethyl)-

HRID 1065673Notes

Reaction equation

HRID 1065673 reaction equation
C[O:2][C:3](=O)[C:4]([CH:10]([F:12])[F:11])([NH2:9])[CH2:5][CH2:6][CH2:7][NH2:8].C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl.C[O-].[Na+]>CO>[NH2:9][C:4]1([CH:10]([F:12])[F:11])[CH2:5][CH2:6][CH2:7][NH:8][C:3]1=[O:2]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 131712630HCID 131712630, compound

Product 1

HCID 5746312-Piperidinone, 3-amino-3-(difluoromethyl)-

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of methyl-2-difluoromethyl-2,5-diamino-pentanoate-dihydrochloride (2.7 g) in dry methanol (30 ml) is added under nitrogen 2 equivalents of sodium methylate in methanol (0.46 g of sodium in 20 ml of methanol). The reaction mixture is stirred for 3 hours at room temperature then the solvent is evaporated under reduced pressure. The residue is extracted with ether to yield crude 3-amino-3-difluoromethyl-2-piperidone which is purified either by crystallization from CHCl3 /pentane: (mp: 149° C.) or by distillation (bp: 135° C./0.05 mmHg).

Workup

  1. customthe solvent is evaporated under reduced pressure
  2. extractionThe residue is extracted with ether

Sources & evidence

ORD record
ord-c4e9b2a87ba74ace952b02a3f3df1e6d
Source dataset
uspto-grants-1982_05
Patent number
US04330559

Reaction notes

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