Phenyl chloroformate → HCID 20343997, compound

HRID 2049878Notes

Reaction equation

HRID 2049878 reaction equation
[C:1]([C:3]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[S: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(C1(C2C=CC=CC=2SC2C=CC=CC=2)CCN(C)CC1)#N.Cl[C:47]([O:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)=[O:48]>C(Cl)Cl>[C:1]([C:3]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[S:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:8][CH2:7][N:6]([C:47]([O:49][C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)=[O:48])[CH2:5][CH2:4]1)#[N:2]

Participants

5

Reactant 3

HCID 15891Phenyl chloroformateHCID 20343959HCID 20343959, compoundHCID 20343960HCID 20343960, compound

Product 1

HCID 20343997HCID 20343997, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2.5 g of 4-cyano-1-methyl-4-(2-phenylthiophenyl)piperidine, free base of Example 3, 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 saturated sodium chloride solution, dried and evaporated. The residue is chromatographed through a silica gel column, first with an ether eluant and then with an ether-hexane (1:1) mixture eluant, until there is no indication of contamination by thin layer chromatography. Thereafter, the product is chromatographed through the same absorbent, ether eluant to provide 4-cyano-1-phenoxycarbonyl-4-(2-phenylthiophenyl)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 saturated sodium chloride solution
  5. customdried
  6. customevaporated
  7. customThe residue is chromatographed through a silica gel column, first with an ether eluant
  8. customThereafter, the product is chromatographed through the same absorbent, ether eluant

Sources & evidence

ORD record
ord-951dd259af7841f9bb0e5aacd22d30f1
Source dataset
uspto-grants-1980_04
Patent number
US04198419

Reaction notes

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