Potassium Hydroxide → 1-Benzyl-4-methylamino-3,3-dimethylpiperidine

HRID 746866Notes

Reaction equation

HRID 746866 reaction equation
[OH-].[K+].Cl.CN.[CH2:6]([N:13]1[CH2:18][CH2:17][C:16](=O)[C:15]([CH3:21])([CH3:20])[CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:22]([BH3-])#[N:23].[Na+]>CO>[CH2:6]([N:13]1[CH2:18][CH2:17][CH:16]([NH:23][CH3:22])[C:15]([CH3:21])([CH3:20])[CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 14797Potassium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 6364545Methylamine hydrochlorideHCID 97944131-Benzyl-3,3-dimethylpiperidin-4-one

Product 1

HCID 222788881-Benzyl-4-methylamino-3,3-dimethylpiperidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium hydroxide (12.85 g, 230 mmol) was added to the stirred solution of methylamine hydrochloride (15.5 g, 230.0 mmol) in methanol (100 ml) and stirring was continued for 30 min at 30° C. 1-Benzyl-3,3-dimethyl-4-piperidone (5 g, 23.0 mmol), was added to the resulting mixture and stirred for 6 hr. Sodium cyanoborohydride (1.45 g, 23.0 mmol) was added to it and reaction mixture was stirred for 15 hr. The reaction mixture was concentrated to dryness, triturated with water, extracted with chloroform, dried (Na2SO4) and concentrated to give 1-benzyl-4-methylamino-3,3-dimethylpiperidine. Yield 5.3 g (99%), C15H24N2, m/z 233 (M+1), PMR (CDCl3): 0.9 (s, 3H), 1.0 (s, 3H), 1.38 (m, 2H), 1.54 (bs, 1H, D2O exchangeable), 1.68-2.1 (m, 4H), 2.4 (s, 3H), 2.86 (m, 1H), 3.4 (dd, 2H), 7.3 (m, 5H).

Workup

  1. stirringstirred for 6 hr
  2. stirringwas stirred for 15 hr
  3. concentrationThe reaction mixture was concentrated to dryness
  4. customtriturated with water
  5. extractionextracted with chloroform
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c50f0bc546664eeea362f2ccc96f2f39
Source dataset
uspto-grants-2008_07
Patent number
US07393957B2

Reaction notes

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