Acetic Acid → HCID 22278860, compound

HRID 1865262Notes

Reaction equation

HRID 1865262 reaction equation
C=O.N[CH:4]1[CH2:9][CH2:8][N:7]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:6][C:5]1([CH2:18][CH3:19])[CH3:17].[C:20]([BH3-])#[N:21].[Na+].[C:24](O)(=O)C>CO>[CH2:10]([N:7]1[CH2:8][CH2:9][CH:4]([N:21]([CH3:20])[CH3:24])[C:5]([CH2:18][CH3:19])([CH3:17])[CH2:6]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 222788954-Amino-1-benzyl-3-ethyl-3-methylpiperidine

Product 1

HCID 22278860HCID 22278860, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Paraformaldehyde (10 g) was added to the stirred solution of 4-amino-1-benzyl-3-ethyl-3-methylpiperidine (8.0 g, 34 mmol) in methanol (100 ml) at 0° C. and sodium cyanoborohydride (2.14 g, 34 mmol) was added to it. Then, acetic acid (2 ml) was added to the resulting mixture and stirring was continued for 24 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 give 1-benzyl-4-dimethylamino-3-ethyl-3-methylpiperidine. Yield 6 g (67%), C17H28N2, m/z 261 (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

Sources & evidence

ORD record
ord-78c01f015098430eb2fd00b243456697
Source dataset
uspto-grants-2009_12
Patent number
US07626032B2

Reaction notes

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