Acetic Acid → HCID 22278872, compound

HRID 746871Notes

Reaction equation

HRID 746871 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-66ab2a981c3840b880a76faa2899cb34
Source dataset
uspto-grants-2008_07
Patent number
US07393957B2

Reaction notes

Loading…