Ethyl Acrylate → 1-Piperidinepropanoic acid, 3-(ethoxycarbonyl)-, ethyl ester

HRID 37808

Reaction equation

HRID 37808 reaction equation
[NH:1]1[CH2:11][CH2:10][CH2:9][CH:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:2]1.[C:12]([O:16][CH2:17][CH3:18])(=[O:15])[CH:13]=[CH2:14]>>[CH2:17]([O:16][C:12](=[O:15])[CH2:13][CH2:14][N:1]1[CH2:11][CH2:10][CH2:9][CH:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:2]1)[CH3:18]

Participants

3

Reactant 2

HCID 8821Ethyl AcrylateHCID 98969Ethyl nipecotate

Product 1

HCID 115651151-Piperidinepropanoic acid, 3-(ethoxycarbonyl)-, ethyl ester

Conditions

Temperature
80 °C

Procedure

A 25 mL round-bottom flask was charged with ethyl nipecotate (8.0 mL, 51.5 mmol, Aldrich) and ethyl acrylate (6.0 mL, 55.4 mmol, Aldrich). The flask was purged with nitrogen and the mixture was heated to 80° C. for 20 hours. The excess ethyl acrylate was removed under reduced pressure. The remaining residue was purified by distillation (0.9 Ton, 122° C.) to provide the title compound: 1H NMR (400 MHz, CDCl3) δ ppm 1.23-1.27 (m, 6H), 1.41-1.59 (m, 2H), 1.69-1.74 (m, 1H), 1.90-1.94 (m, 1H), 2.05 (td, J=10.9, 2.9 Hz, 1H), 2.05 (t, J=10.7 Hz, 1H), 2.46-2.56 (m, 3H), 2.69-2.76 (m, 3H), 2.95-2.98 (m, 1H), 4.10-4.16 (m, 4H); 13C NMR (100 MHz, CDCl3) δ ppm 14.14, 14.15, 24.51, 26.78, 32.61, 41.80, 53.37, 53.79, 55.12, 60.28, 60.23, 172.50, 174.03; MS (DCI/NH3) m/z 258 (M+H)+.

Workup

  1. customThe flask was purged with nitrogen
  2. customThe excess ethyl acrylate was removed under reduced pressure
  3. distillationThe remaining residue was purified by distillation (0.9 Ton, 122° C.)

Sources & evidence

ORD record
ord-d33cd4c1758c4021a4d601fa24dcd8c8
Source dataset
uspto-grants-2013_09
Patent number
US08524703B2

Linked notes

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