Ethyl chloroformate → HCID 53960004, compound

HRID 1973847Notes

Reaction equation

HRID 1973847 reaction equation
[CH3:1][O:2][CH2:3][C:4]1([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:6][CH2:5]1.[C:27](Cl)(=[O:31])[O:28][CH2:29][CH3:30]>>[CH2:29]([O:28][C:27]([N:20]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:4]1([CH2:3][O:2][CH3:1])[CH2:5][CH2:6][N:7]([C:10]([O:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[O:11])[CH2:8][CH2:9]1)=[O:31])[CH3:30]

Participants

3

Reactant 2

HCID 10928Ethyl chloroformateHCID 54398456HCID 54398456, compound

Product 1

HCID 53960004HCID 53960004, compoundYield 83.5%

Conditions

Temperature
110 °C

Procedure

A mixture of 14.2 parts of (phenylmethyl) 4-(methoxymethyl)-4-(phenylamino)-1-piperidinecarboxylate and 170.2 parts of ethyl carbonochloridate is stirred and refluxed for 16 hours in an oil-bath at 110° C. The reaction mixture is evaporated and the residue is dissolved in 225 parts of trichloromethane. The solution is washed twice with water, dried, filtered and evaporated. The residue is dissolved in methylbenzene and the latter is evaporated again, yielding 14.2 parts (83.5%) of (phenylmethyl) 4-[(ethoxycarbonyl)phenylamino]-4-(methoxymethyl)-1-piperidinecarboxylate as a residue.

Workup

  1. customThe reaction mixture is evaporated
  2. dissolutionthe residue is dissolved in 225 parts of trichloromethane
  3. washThe solution is washed twice with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. dissolutionThe residue is dissolved in methylbenzene
  8. customthe latter is evaporated again

Sources & evidence

ORD record
ord-8c8c45a2afb34b2ab80b9cb0946891d1
Source dataset
uspto-grants-1976_12
Patent number
US03998834

Reaction notes

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