Water → (S)-1-Benzyl-3-methylpiperidine-3-carboxylic acid ethyl ester

HRID 2366025Notes

Reaction equation

HRID 2366025 reaction equation
[CH2:1]([O:3][C:4]([C@@:6]1([CH3:12])[CH2:11][CH2:10][CH2:9][NH:8][CH2:7]1)=[O:5])[CH3:2].[CH2:13](Cl)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH2:1]([O:3][C:4]([C@@:6]1([CH3:12])[CH2:11][CH2:10][CH2:9][N:8]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 23389262(S)-Ethyl 3-methylpiperidine-3-carboxylate

Product 1

HCID 66727374(S)-1-Benzyl-3-methylpiperidine-3-carboxylic acid ethyl esterYield 92.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(S)-3-Methylpiperidine-3-carboxylic acid ethyl ester (1.16 g, 6.8 mmol), benzyl chloride (0.82 ml, 7.1 mmol), K2CO3 (1.22 g, 8.8 mmol) and KI (0.056 g) were stirred and heated in DMF (50 ml) for 2.5 h. The cooled solution was poured into water and extracted with EtOAc (3×50 ml). The combined extracts were washed several times with water and finally with brine. Drying, filtering and evaporation of the solvent gave 1.64 g of the target compound as a yellowish oil.

Workup

  1. extractionextracted with EtOAc (3×50 ml)
  2. washThe combined extracts were washed several times with water
  3. customDrying
  4. filtrationfiltering
  5. customevaporation of the solvent

Sources & evidence

ORD record
ord-f3feb6ee413e498e96bc62dc0bfebb84
Source dataset
uspto-grants-2014_04
Patent number
US08697723B2

Reaction notes

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