1-Chloroethyl chloroformate → HCID 10245962, compound

HRID 1613296Notes

Reaction equation

HRID 1613296 reaction equation
ClC(OC(Cl)C)=O.C([N:15]1[CH2:20][CH:19]=[C:18]([CH2:21][NH:22][C:23](=[O:38])[C:24]([CH:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)([OH:31])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:17][CH2:16]1)C1C=CC=CC=1>C(Cl)Cl>[NH:15]1[CH2:16][CH:17]=[C:18]([CH2:21][NH:22][C:23](=[O:38])[C:24]([CH:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)([OH:31])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:19][CH2:20]1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 10251469HCID 10251469, compound

Product 1

HCID 10245962HCID 10245962, compoundYield 16.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1-chloroethyl chloroformate (0.53 ml) in methylene chloride (5 ml) was added dropwise to a solution of N-(1-benzyl-1,2,3,6-tetrahydropyridin-4-yl)methyl-2-cyclohexyl-2-hydroxy-2-phenylacetamide (1.50 g) in methylene chloride (25 ml) below 7° C. After being refluxed for 1 hour, the reaction mixture was evaporated in vacuo. To the residue was added methanol (20 ml) and the mixture was refluxed for 1.5 hours. The reaction mixture was evaporated in vacuo, and to the residue was added 1N aqueous solution of sodium hydroxide. The mixture was extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was recrystallized from a mixture of 2-propanol and ethanol to give N-(1,2,3,6-tetrahydropyridin-4-yl)methyl-2-cyclohexyl-2-hydroxy-2-phenylacetamide (0.19 g).

Workup

  1. temperatureAfter being refluxed for 1 hour
  2. customthe reaction mixture was evaporated in vacuo
  3. additionTo the residue was added methanol (20 ml)
  4. temperaturethe mixture was refluxed for 1.5 hours
  5. customThe reaction mixture was evaporated in vacuo
  6. additionto the residue was added 1N aqueous solution of sodium hydroxide
  7. extractionThe mixture was extracted with ethyl acetate
  8. washThe extract was washed with brine
  9. dry with materialdried over magnesium sulfate
  10. customevaporated in vacuo
  11. customThe residue was recrystallized from a mixture of 2-propanol and ethanol

Sources & evidence

ORD record
ord-f72c7bfb113e4bb185f8d74642a526af
Source dataset
uspto-grants-1993_03
Patent number
US05192779

Reaction notes

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