Acetic Acid → HCID 22278872, compound

HRID 1063302Notes

Reaction equation

HRID 1063302 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([CH3:18])[CH3:17].[C:19]([BH3-])#[N:20].[Na+].[C:23](O)(=O)C>CO>[CH2:10]([N:7]1[CH2:8][CH2:9][CH:4]([N:20]([CH3:19])[CH3:23])[C:5]([CH3:18])([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 102361061-Benzyl-3,3-diMethyl-piperidin-4-aMine

Product 1

HCID 22278872HCID 22278872, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Formaldehyde solution (47%, 10 g) was added to the stirred solution of 4-amino-1-benzyl-3,3-dimethylpiperidine (2.0 g, 9.2 mmol) in methanol (20 ml) at 0° C. and sodium cyanoborohydride (0.5 g, 9.2 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-3,3-dimethylpiperidine. Yield 1.9 g (84%), C16H26N2, m/z 247 (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-cd6069891db04eaab31785034f092653
Source dataset
uspto-grants-2005_11
Patent number
US06964966B2

Reaction notes

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