Dimethylformamide → HCID 52139959, compound

HRID 657627Notes

Reaction equation

HRID 657627 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][CH:8]1[CH2:13][CH:12]([CH3:14])[CH2:11][NH:10][CH2:9]1.CN(C)C=O.[CH2:20](Cl)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[CH2:20]([N:10]1[CH2:11][C@@H:12]([CH3:14])[CH2:13][C@H:8]([CH3:7])[CH2:9]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 1182593,5-Dimethylpiperidine

Product 1

HCID 52139959HCID 52139959, compoundYield 14.8%

Procedure

A suspension of potassium carbonate (83 g) in a mixture of benzyl chloride (37 g), 3,5-dimethylpiperidine (30 g of acommercial mixture of cis and trans isomers) and N,N-dimethylformamide (200 mL) is stirred for 15 h at a temperature close to 60° C. The mixture is filtered, concentrated under reduced pressure and diluted in ethyl acetate. The organic phase is washed with water, dried over magnesium sulphate, concentrated under reduced pressure and purified by chromatography over silica gel with a mixture diethyl oxide/ligroin/triethylamine 20/80/1 as eluent to give 8 g of trans-1-benzyl-3,5-dimethylpiperidine as a colourless oil used without further purification.

Workup

  1. customclose to 60° C
  2. filtrationThe mixture is filtered
  3. concentrationconcentrated under reduced pressure
  4. additiondiluted in ethyl acetate
  5. washThe organic phase is washed with water
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated under reduced pressure
  8. custompurified by chromatography over silica gel with a mixture diethyl oxide/ligroin/triethylamine 20/80/1 as eluent

Sources & evidence

ORD record
ord-01295fa1732a4e6bb107de31de19b999
Source dataset
uspto-grants-2011_12
Patent number
US08076329B2

Reaction notes

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