Acetic Acid → 1-Carbethoxy-4-dimethylamino-3-methylpiperidine

HRID 746855Notes

Reaction equation

HRID 746855 reaction equation
C=O.N[CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:6][CH:5]1[CH3:15].[C:16]([BH3-])#[N:17].[Na+].[C:20](O)(=O)C>CO>[C:10]([N:7]1[CH2:8][CH2:9][CH:4]([N:17]([CH3:16])[CH3:20])[CH:5]([CH3:15])[CH2:6]1)([O:12][CH2:13][CH3:14])=[O:11]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 22278886Ethyl 4-amino-3-methylpiperidine-1-carboxylate

Product 1

HCID 222788651-Carbethoxy-4-dimethylamino-3-methylpiperidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Paraformaldehyde (5.1 g) was added to the stirred solution of 4-amino-1-carbethoxy-3-methylpiperidine (3.5 g, 18.8 mmol) in methanol (100 ml) at 0° C. and sodium cyanoborohydride (1.7 g, 27.0 mmol) was added to it. Then, acetic acid (1 ml) was added to the resulting mixture and stirring was continued for 96 hr at ambient temperature. The reaction mixture was concentrated to dryness, triturated with water, acidified with conc. HCl (pH 3˜4) and extracted with ethyl acetate to remove impurities. The aqueous layer was basified with 1 M sodium hydroxide solution (pH ˜10) and extracted with ethyl acetate. Ethyl acetate extract was dried (Na2SO4) and concentrated to dryness to give 1-carbethoxy-4-dimethylamino-3-methylpiperidine. Yield 3.5 g (88%), C11H22N2O2, m/z 215 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customtriturated with water
  3. extractionextracted with ethyl acetate
  4. customto remove impurities
  5. extractionextracted with ethyl acetate
  6. extractionEthyl acetate extract
  7. dry with materialwas dried (Na2SO4)
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-3d24d65518384ac2936c5b061b0cb5fb
Source dataset
uspto-grants-2008_07
Patent number
US07393957B2

Reaction notes

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