Ethyl chloroformate → O4-methyl O1-(phenylmethyl) 4-[(ethoxycarbonyl)phenylamino]-1,4-piperidinedicarboxylate

HRID 1448337Notes

Reaction equation

HRID 1448337 reaction equation
[C:1]1([NH:7][C:8]2([C:24]([O:26][CH3:27])=[O:25])[CH2:13][CH2:12][N:11]([C:14]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:15])[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:28](Cl)(=[O:32])[O:29][CH2:30][CH3:31]>>[CH2:30]([O:29][C:28]([N:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:8]1([C:24]([O:26][CH3:27])=[O:25])[CH2:9][CH2:10][N:11]([C:14]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[O:15])[CH2:12][CH2:13]1)=[O:32])[CH3:31]

Participants

3

Reactant 2

HCID 10928Ethyl chloroformateHCID 86734314HCID 86734314, compound

Product 1

HCID 86734315O4-methyl O1-(phenylmethyl) 4-[(ethoxycarbonyl)phenylamino]-1,4-piperidinedicarboxylate

Conditions

Temperature
110 °C

Procedure

A mixture of 14.8 parts of O4 -methyl O1 -(phenylmethyl) 4-(phenylamino)-1,4-piperidinedicarboxylate and 203 parts of ethyl carbonochloridate is stirred and refluxed for 24 hours in an oil-bath at 110° C. The reaction mixture is evaporated and the residue is dissolved in trichloromethane. The solution is washed twice with water, dried, filtered and evaporated, yielding 16.2 parts of O4 -methyl O1 -(phenylmethyl) 4-[(ethoxycarbonyl)phenylamino]-1,4-piperidinedicarboxylate as a residue.

Workup

  1. customThe reaction mixture is evaporated
  2. dissolutionthe residue is dissolved in trichloromethane
  3. washThe solution is washed twice with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-74cf6a8506e542efb1d67382c437f082
Source dataset
uspto-grants-1979_12
Patent number
US04179569

Reaction notes

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