Cyclohexylamine → HCID 70269258, compound

HRID 1872752Notes

Reaction equation

HRID 1872752 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH:7]1([NH2:13])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.Br[CH2:15][C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]>C(Cl)Cl>[C:16]([OH:18])(=[O:17])[CH3:15].[CH2:19]([NH:13][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7965CyclohexylamineHCID 11430Potassium CarbonateHCID 62576Benzyl bromoacetate

Product 1

HCID 70269258HCID 70269258, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice-water cooled solution of 65.8 ml of methylene chloride and 18.2 g of potassium carbonate is added 11.3 ml (98.7 mmol) of cyclohexylamine. To this mixture is added dropwise, over a period of 1 hour, a mixture of 5.21 ml (32.9 mmol) of benzyl 2-bromo-acetate and 65.8 ml of methylene chloride. The resultant hazy, white reaction mixture is then stirred at ice-water temperature for 2.5 hours and then at room temperature for 2.5 days. The resultant opaque, white reaction mixture is then partitioned between methylene chloride and water, and the methylene chloride layer is extracted. The aqueous layer is then washed twice with 50 ml portions of methylene chloride and the combined methylene chloride layers are washed with saturated aqueous sodium chloride and dried over sodium sulfate. The solution is then filtered and concentrated to yield a clear yellow liquid which is purified via column chromatography employing a mixture of hexane and ethyl acetate (1:1 ratio) as the eluant to obtain the desired compound as a clear, very light yellow liquid.

Workup

  1. additionTo this mixture is added dropwise, over a period of 1 hour
  2. customThe resultant opaque, white reaction mixture is then partitioned between methylene chloride and water
  3. extractionthe methylene chloride layer is extracted
  4. washThe aqueous layer is then washed twice with 50 ml portions of methylene chloride
  5. washthe combined methylene chloride layers are washed with saturated aqueous sodium chloride
  6. dry with materialdried over sodium sulfate
  7. filtrationThe solution is then filtered
  8. concentrationconcentrated
  9. customto yield a clear yellow liquid which
  10. customis purified via column chromatography
  11. additiona mixture of hexane and ethyl acetate (1:1 ratio) as the eluant

Sources & evidence

ORD record
ord-5b4be6767fec45889db1427a71eb5378
Source dataset
uspto-grants-2000_08
Patent number
US06110949

Reaction notes

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