4-Benzylpiperidine → Ethyl 3-(4-benzylpiperidin-1-yl)butyrate

HRID 1861775Notes

Reaction equation

HRID 1861775 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:14]([O:19][CH2:20][CH3:21])(=[O:18])/[CH:15]=[CH:16]/[CH3:17]>C(O)(C)C>[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH:16]([CH3:17])[CH2:15][C:14]([O:19][CH2:20][CH3:21])=[O:18])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 317384-BenzylpiperidineHCID 429065Ethyl trans-crotonate

Product 1

HCID 18621512Ethyl 3-(4-benzylpiperidin-1-yl)butyrateYield 79%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 4-benzyl piperidine (0.50 mL, 2.8 mmol) and ethyl crotonate (0.46 mL, 3.4 mmol) in isopropanol (10 mL) was refluxed for 24 h and was concentrated in vacuo. The crude compound was purified by filtration on silica gel using CH2Cl2/MeOH as solvent to afford the title compound as a pale yellow oil (0.64 g, 74%): 1H NMR (CDCl3) δ1.09 (d, J=6.6 Hz, 3H), 1.30 (t, J=6.9 Hz, 3H), 1.20-1.40 (m, 2H), 1.45-1.61 (m, 1H), 1.68 (bd, J=12.3 Hz, 2H), 2.10-2.35 (m, 3H), 2.57 (d, J=6.9 Hz, 2H), 2.50-2.70 (m, 1H), 2.82 (bd, J=10.8 Hz, 2H), 3.15-3.30 (m, 1H), 4.18 (q, J=6.9 Hz, 2H), 7.18 (d, J=7.2 Hz, 2H), 7.24 (m, 1H), 7.32 (t, J=6.9 Hz, 2H).

Workup

  1. concentrationwas concentrated in vacuo
  2. filtrationThe crude compound was purified by filtration on silica gel

Sources & evidence

ORD record
ord-f459b87e99194885b20581a2ab802be0
Source dataset
uspto-grants-2003_03
Patent number
US06534522B2

Reaction notes

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