Cyclohexyl methyl ketone → 1-Cyclohexyl-3-dimethylamino-propenone

HRID 460700

Reaction equation

HRID 460700 reaction equation
[CH3:1][C:2]([CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)=O.C([O:14][CH:15](N(C)C)[N:16]([CH3:18])[CH3:17])(C)(C)C>>[CH3:17][N:16]([C:15](/[CH:1]=[CH:2]/[CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)=[O:14])[CH3:18]

Participants

3

Reactant 2

HCID 13207Cyclohexyl methyl ketoneHCID 79885tert-Butoxy bis(dimethylamino)methane

Product 1

HCID 110952411-Cyclohexyl-3-dimethylamino-propenoneYield 93%

Conditions

Temperature
60 °C

Procedure

A mixture of 3.0 g (23.8 mmol) of cyclohexyl methyl ketone and 4.56 g (26.2 mmol) of t-butoxybis(dimethylamino)methane (Bredereck's reagent) was stirred at 60° C. overnight. The reaction mixture was then concentrated to give 4.0 g (93% yield) of 1-cyclohexyl-3-dimethylamino-propenone as an orange oil as indicated by 1H NMR. This product was used in the next reaction without any further purification.

Workup

  1. concentrationThe reaction mixture was then concentrated

Sources & evidence

ORD record
ord-cbb6055354164bfe8509e4c4b6195761
Source dataset
uspto-grants-2007_03
Patent number
US07196111B2

Linked notes

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