N,N-Dimethylcyclohexylamine → 3-Hydroxy-2-cyclobuten-1-one-cyclohexyldimethylammonium salt

HRID 892649

Reaction equation

HRID 892649 reaction equation
[CH3:1][N:2]([CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)[CH3:3].[C:10]1(=[O:15])[CH2:13][C:12](=[O:14])[CH2:11]1>C(OCC)(=O)C>[CH:4]1([NH+:2]([CH3:3])[CH3:1])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.[OH:15][C:10]1[CH2:13][C:12](=[O:14])[CH:11]=1

Participants

4

Reactant 2

HCID 7415N,N-DimethylcyclohexylamineHCID 27357Cyclobutane-1,3-dione

Product 1

HCID 198960323-Hydroxy-2-cyclobuten-1-one-cyclohexyldimethylammonium saltYield 87.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 3.21 g of N,N-dimethylcyclohexylamine (99 percent; 25.0 mmol) in 10 g of ethyl acetate was instilled in a suspension of 2.1 g of 1,3-cyclobutanedione (91.9 percent; 23.0 mmol) in 40 g of ethyl acetate at 20° C. in 15 minutes. After 1 hour of stirring at room temperature, the suspension was filtered and dried under vacuum. 4.27 g of the title product with a purity of 94.8 percent (according to HPLC), corresponding to a yield of 83.3 percent, relative to the cyclobutanedione, was obtained. Data for the title compound was:

Workup

  1. filtrationthe suspension was filtered
  2. customdried under vacuum

Sources & evidence

ORD record
ord-301a84d73f9d4c21be048768e7f4a8d3
Source dataset
uspto-grants-1992_06
Patent number
US05118847

Linked notes

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