Phenyl chloroformate → HCID 12694085, compound

HRID 647535Notes

Reaction equation

HRID 647535 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[S:15][C:8]3([CH2:13][CH2:12][N:11](C)[CH2:10][CH2:9]3)[C:6]=2[CH:7]=1.Cl[C:24]([O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:25]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:16]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[S:15][C:8]3([CH2:13][CH2:12][N:11]([C:24]([O:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[O:25])[CH2:10][CH2:9]3)[C:6]=2[CH:7]=1

Participants

4

Reactant 2

HCID 15891Phenyl chloroformateHCID 12694062HCID 12694062, compound

Product 1

HCID 12694085HCID 12694085, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.3 g of 6-fluoro-1,3-dihydro-1'-methyl-3-phenylspiro[benzo(c)thiophene-1,4'-piperidine] and 0.3 g of phenyl chloroformate in 10 ml of methylene chloride which was previously stirred at ambient temperature for 16 hours is sequentially quenched with water, washed with 10% sodium hydroxide and dried. The reaction mixture is concentrated under vacuum leaving a viscous oil which crystallized with standing. The solid product is recrystallized from an ether-pentane mixture to give prisms, m.p. 156°-158° C. of 6-fluoro-1,3-dihydro-3-phenyl-1'-phenoxycarbonylspiro[benzo(c)thiophene-1,4'-piperidine].

Workup

  1. customis sequentially quenched with water
  2. washwashed with 10% sodium hydroxide
  3. customdried
  4. concentrationThe reaction mixture is concentrated under vacuum
  5. customleaving a viscous oil which
  6. customcrystallized
  7. customThe solid product is recrystallized from an ether-pentane mixture

Sources & evidence

ORD record
ord-3c6301cad984425c96d2f1f9038bcff9
Source dataset
uspto-grants-1983_10
Patent number
US04409229

Reaction notes

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