Phenyl chloroformate → HCID 12694091, compound

HRID 647537Notes

Reaction equation

HRID 647537 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[S:22][C:15]3([CH2:20][CH2:19][N:18](C)[CH2:17][CH2:16]3)[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]2=3)=[CH:4][CH:3]=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:7]=[CH:6][C:5]([CH:8]2[S:22][C:15]3([CH2:16][CH2:17][N:18]([C:24]([O:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[O:25])[CH2:19][CH2:20]3)[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]2=3)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 15891Phenyl chloroformateHCID 12694072HCID 12694072, compound

Product 1

HCID 12694091HCID 12694091, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(4-fluorophenyl)-1,3-dihydro-1'-methylspiro[benzo(c)thiophene-1,4'-piperidine] of Example 27 (3.6 g), 2.1 g of phenyl chloroformate in 100 ml of CH2Cl2 is stirred at room temperature for 64 hours. The solution is washed with 10% aqueous NaOH, water, and dried over MgSO4. Evaporation under reduced pressure affords a crystalline residue, m.p. 198°-200° C. Recrystallization of the crude product from acetone-pentane gives granular crystals, m.p. 200°-201° C. for 3-(4-fluorophenyl)-1,3-dihydro-1'-phenoxycarbonylspiro[benzo(c)thiophene-1,4'-piperidine].

Workup

  1. washThe solution is washed with 10% aqueous NaOH, water
  2. dry with materialdried over MgSO4
  3. customEvaporation under reduced pressure
  4. customaffords a crystalline residue, m.p. 198°-200° C
  5. customRecrystallization of the crude product from acetone-pentane

Sources & evidence

ORD record
ord-9cf181d784244fa9a19a8158646d726b
Source dataset
uspto-grants-1983_10
Patent number
US04409229

Reaction notes

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