Cyclohexylamine → N-Cyclohexylacetoacetamide

HRID 1055245

Reaction equation

HRID 1055245 reaction equation
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:8]=[C:9]1[O:13][C:11](=[O:12])[CH2:10]1>O1CCCC1>[CH:1]1([NH:7][C:11](=[O:12])[CH2:10][C:9](=[O:13])[CH3:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 7965CyclohexylamineHCID 12661Diketene

Product 1

HCID 70805N-CyclohexylacetoacetamideYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 23.6 g (0.24 mol) of cyclohexylamine in 50 ml tetrahydrofuran was added dropwise to a solution of 20 g of diketene (0.24 mol) in 200 ml tetrahydrofuran at −5 to 0° C. After 1 h stirring at 0° C. no more starting material was detected by thin layer chromatography. The reaction mixture was evaporated and the residue is recrystallized from 100 ml of ethyl acetate. This gave 30.0 g (0.16 mol, 69% yield) of a white solid.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue is recrystallized from 100 ml of ethyl acetate

Sources & evidence

ORD record
ord-51cb5184cb2c4eb6a2870b7235418c60
Source dataset
uspto-grants-2016_07
Patent number
US09394324B2

Linked notes

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