Benzyl chloroformate → Phenylmethyl 2-[2-(acetyloxy)ethyl]-4-morpholinecarboxylate

HRID 1608218Notes

Reaction equation

HRID 1608218 reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH:7]1[O:12][CH2:11][CH2:10][N:9](CC2C=CC=CC=2)[CH2:8]1)(=[O:3])[CH3:2].Cl[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22]>C(#N)C>[C:1]([O:4][CH2:5][CH2:6][CH:7]1[O:12][CH2:11][CH2:10][N:9]([C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])[CH2:8]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 19848591HCID 19848591, compound

Product 1

HCID 19848607Phenylmethyl 2-[2-(acetyloxy)ethyl]-4-morpholinecarboxylateYield 72.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-(2-acetoxyethyl)-4-benzylmorpholine (29.1 g) in acetonitrile (200 ml) is dropwise added benzyl chloroformate (24.4 g). The reaction mixture is refluxed for 30 minutes, cooled and evaporated under reduced pressure. The residue is chromatographed on silica gel. The eluate with hexane is discarded, and the subsequent eluates with hexane-chloroform (1:1) are pooled and evaporated to give the title compound (24.5 g) as an oil.

Workup

  1. temperatureThe reaction mixture is refluxed for 30 minutes
  2. temperaturecooled
  3. customevaporated under reduced pressure
  4. customThe residue is chromatographed on silica gel
  5. customevaporated

Sources & evidence

ORD record
ord-2961411c83ec4e38a426bdaa666b84c8
Source dataset
uspto-grants-1989_09
Patent number
US04870074

Reaction notes

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