Piperidine → Ethyl 4-(piperidin-1-yl)butanoate

HRID 241012Notes

Reaction equation

HRID 241012 reaction equation
Br[CH:2]([CH3:9])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[NH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1>CN(C)C=O.C(OCC)(=O)C>[N:10]1([CH2:9][CH2:2][CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

5

Reactant 2

HCID 8082PiperidineHCID 95424Butanoic acid, 3-bromo-, ethyl ester

Product 1

HCID 14044356Ethyl 4-(piperidin-1-yl)butanoateYield 81.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 3-bromobutanoate (6.0 mL, 42 mmol) in N,N-dimethylformamide (20 mL) at 0° C. was added piperidine (8.0 mL, 80 mmol) and the mixture was warmed to room temperature then stirred 16 h. The reaction mixture was diluted with ethyl acetate (200 mL) and washed with a solution of brine and 2.0M aqueous sodium hydroxide (4:1 v/v). The organic phase was then dried over anhydrous sodium sulfate, filtered and concentrated to give ethyl 4-piperidin-1-ylbutanoate (6.8 g, 81% yield) as brown oil. MS (EI) for C11H21NO2: 200 (MH+).

Workup

  1. washwashed with a solution of brine and 2.0M aqueous sodium hydroxide (4:1 v/v)
  2. dry with materialThe organic phase was then dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ae4805885de942df8959605d04797bae
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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