Hydroquinone → Ethyl 3-(2,2-dimethylpropyl)-2-piperidin-1-ylcyclobutanecarboxylate

HRID 1912064Notes

Reaction equation

HRID 1912064 reaction equation
[CH3:1][C:2]([CH3:13])([CH3:12])[CH2:3][CH:4]=[CH:5][N:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.[C:14]([O:18][CH2:19][CH3:20])(=[O:17])[CH:15]=[CH2:16].C1(C=CC(O)=CC=1)O>C(#N)C>[CH3:1][C:2]([CH3:13])([CH3:12])[CH2:3][CH:4]1[CH2:16][CH:15]([C:14]([O:18][CH2:19][CH3:20])=[O:17])[CH:5]1[N:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 785HydroquinoneHCID 8821Ethyl AcrylateHCID 866750371-(4,4-Dimethyl-1-pentenyl)piperidine

Product 1

HCID 71114785Ethyl 3-(2,2-dimethylpropyl)-2-piperidin-1-ylcyclobutanecarboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

1-(4,4-Dimethyl-1-pentenyl)piperidine (1146 g) and acetonitrile (910 mL) were mixed. After an addition of ethyl acrylate (549 mL) and hydroquinone (553 mg) to the mixture, the mixture was stirred at 90° C. overnight. The reaction mixture was concentrated in vacuo to give the title compound (1470 g) as a crude product.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-11adb3d2d20e4c44a3a8e3c23eebcdf5
Source dataset
uspto-grants-2013_12
Patent number
US08604069B2

Reaction notes

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