Dichloromethane → HCID 54278868, compound

HRID 634777Notes

Reaction equation

HRID 634777 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][NH:10][CH:11]2[CH2:16][CH2:15][C:14](=[O:17])[CH2:13][CH2:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].Cl[C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26].C(Cl)Cl>O>[CH2:28]([O:27][C:25](=[O:26])[N:10]([CH:11]1[CH2:16][CH2:15][C:14](=[O:17])[CH2:13][CH2:12]1)[CH2:9][CH2:8][CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 15290860HCID 15290860, compound

Product 1

HCID 54278868HCID 54278868, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-(3-phenyl-propylamino)-cyclohexanone (1.9 g, 8.21 mmol), K2CO3 (1.15 g, 8.3 mmol), benzyl chloroformate (1.42 g, 8.3 mmol) and CH2Cl2 (20 ml) was stirred at r.t for 1.5 h. H2O (50 ml) was added, and the mixture was extracted with CH2Cl2. The organic layer was dried (Na2SO4), evaporated and the residue was purified by chromatography (SiO2, CH2Cl2—MeOH 95:5) to give (4-Oxo-cyclohexyl)-(3-phenyl-propyl)-carbamic acid benzyl ester as a yellow oil (2.7 g, 90%, MS: m/e=365(M+)).

Workup

  1. extractionthe mixture was extracted with CH2Cl2
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. customevaporated
  4. customthe residue was purified by chromatography (SiO2, CH2Cl2—MeOH 95:5)

Sources & evidence

ORD record
ord-f923cf71a69f49d9962423429122fa94
Source dataset
uspto-grants-2001_02
Patent number
US06184236B2

Reaction notes

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