Water → HCID 178515153, compound

HRID 274865Notes

Reaction equation

HRID 274865 reaction equation
[CH2:1]1[CH2:6][CH2:5][CH:4]([NH2:7])[CH2:3][CH2:2]1.C(O[C:11]([CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][C:14]1=O)=[O:12])C.O.[C:21]1(C)[CH:26]=[CH:25][C:24](S(O)(=O)=O)=[CH:23][CH:22]=1.O>C1C=CC=CC=1>[CH:21]1([C:1]2[CH:6]=[C:5]3[C:4]([N:7]=[C:14]4[C:13](=[C:11]3[OH:12])[CH2:18][CH2:17][CH2:16][CH2:15]4)=[CH:3][CH:2]=2)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 962WaterHCID 7965CyclohexylamineHCID 95543Ethyl 2-oxocyclohexanecarboxylateHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 178515153HCID 178515153, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

4-Cyclohexylamine (23.15 g) and 2-ethoxycarbonylcyclohexanone (25.0 g) were stirred in 100 mL of benzene containing 0.20 g of p-toluenesulfonic acid monohydrate. After stirring for 4 hours at room temperature the reaction mixture was refluxed for 3 hours with the separation of water. At the end of this time the benzene was evaporated and the residue was dissolved in 150 mL of phenyl ether and the resultant mixture refluxed for 30 minutes. The product which separated upon cooling was filtered off and washed with ether to give 18.22 g of product which was analytically pure without further purification, mp 292°-295° C.

Workup

  1. customAt the end of this time the benzene was evaporated
  2. dissolutionthe residue was dissolved in 150 mL of phenyl ether
  3. temperaturethe resultant mixture refluxed for 30 minutes
  4. customThe product which separated
  5. temperatureupon cooling
  6. filtrationwas filtered off
  7. washwashed with ether

Sources & evidence

ORD record
ord-df58d21db72c46dd999319972992e098
Source dataset
uspto-grants-1995_02
Patent number
US05391553

Reaction notes

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