Phenyl chloroformate → HCID 20343825, compound

HRID 2049892Notes

Reaction equation

HRID 2049892 reaction equation
[C:1]([C:3]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:8][CH2:7][N:6](C)[CH2:5][CH2:4]1)#[N:2].Cl[C:24]([O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:25]>C(Cl)Cl>[C:1]([C:3]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:8][CH2:7][N:6]([C:24]([O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:25])[CH2:5][CH2:4]1)#[N:2]

Participants

4

Reactant 2

HCID 15891Phenyl chloroformateHCID 20343816HCID 20343816, compound

Product 1

HCID 20343825HCID 20343825, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2.5 g of 4-cyano-1-methyl-4-(2-phenoxyphenyl)piperidine, free base of Example 1, and 1.7 g of phenyl chloroformate in 50 ml of methylene chloride is permitted to stand for 24 hours before being poured onto 100 g of ice. Thereafter, the mixture is extracted with 50 ml of methylene chloride and the organic solution is successively washed twice with 50 ml portions of water, washed once with 40 ml saturated sodium bicarbonate solution, washed once with 40 ml saturated sodium chloride solution, dried and evaporated to provide an oil. The oil is chromatographed (silica gel 60 column, ether eluant) and then chromatographed (silica gel 60 column, ether-hexane (1:1) mixture eluant) until there is no indication of contamination by the layer chromatography. Thereafter, the product is chromatographed through the same absorbent, ether eluant to provide a glassy solid of 4-cyano-1-phenoxycarbonyl-4-(2-phenoxyphenyl)piperidine.

Workup

  1. extractionThereafter, the mixture is extracted with 50 ml of methylene chloride
  2. washthe organic solution is successively washed twice with 50 ml portions of water
  3. washwashed once with 40 ml saturated sodium bicarbonate solution
  4. washwashed once with 40 ml saturated sodium chloride solution
  5. customdried
  6. customevaporated
  7. customto provide an oil
  8. customThe oil is chromatographed (silica gel 60 column, ether eluant)
  9. customchromatographed (silica gel 60 column, ether-hexane (1:1) mixture eluant) until there
  10. customThereafter, the product is chromatographed through the same absorbent, ether eluant

Sources & evidence

ORD record
ord-90e61c8698f04eeb9692240531222714
Source dataset
uspto-grants-1980_04
Patent number
US04198417

Reaction notes

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