Ethyl 4-(4-oxopiperidin-1-yl)benzoate → Ethyl 4-(4-methylenepiperidin-1-yl)benzoate

HRID 1184501Notes

Reaction equation

HRID 1184501 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:18]=[CH:17][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[CH2:19]=C1CCN(C2C=CC=CC=2)CC1>>[CH2:19]=[C:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:18]=[CH:17][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 12717442Ethyl 4-(4-oxopiperidin-1-yl)benzoateHCID 589027244-Methylene-1-phenylpiperidine

Product 1

HCID 16109082Ethyl 4-(4-methylenepiperidin-1-yl)benzoate

Procedure

Using ethyl 4-(4-oxopiperidin-1-yl)benzoate 390B (0.575 g, 2.325 mmol), Wittig olefination was carried out as described for 389A. The title compound was obtained as an off-white crystalline solid (0.338 g, 59.3% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.21-1.38 (m, 3H) 2.18-2.30 (m, 4H) 3.37-3.50 (m, 4H) 4.23 (q, J=7.16 Hz, 2H) 4.78 (s, 2H) 6.95-7.04 (m, 2H) 7.72-7.82 (m, 2H). ESI-MS: m/z 246.2 (M+H)+.

Sources & evidence

ORD record
ord-de179ae5883e4eb697938a6038e5d41c
Source dataset
uspto-grants-2014_03
Patent number
US08669249B2

Reaction notes

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