Phenyl chloroformate → HCID 12694090, compound

HRID 647543Notes

Reaction equation

HRID 647543 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].C(O)(=O)/C=C\C(O)=O.[F:19][C:20]1[CH:21]=[C:22]([CH:26]2[S:40][C:33]3([CH2:38][CH2:37][N:36](C)[CH2:35][CH2:34]3)[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:27]2=3)[CH:23]=[CH:24][CH:25]=1>ClCCl>[F:19][C:20]1[CH:21]=[C:22]([CH:26]2[S:40][C:33]3([CH2:34][CH2:35][N:36]([C:2]([O:4][C:5]4[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=4)=[O:3])[CH2:37][CH2:38]3)[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:27]2=3)[CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 15891Phenyl chloroformateHCID 12694071HCID 12694071, compound

Product 1

HCID 12694090HCID 12694090, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To 5.0 g of phenyl chloroformate in 80 ml of dichloromethane is added 7.89 g of the free base, 3-(3-fluorophenyl)-1,3-dihydro-1'-methylspiro[benzo(c)thiophene-1,4'-piperidine] of Example 55, in 10 ml of dichloromethane over 20 minutes. The reaction mixture is stirred at room temperature for 21 hours, then diluted with 200 ml of dichloromethane. The resultant mixture is washed with two 175 ml portions of 10% aqueous sodium hydroxide solution, two 150 ml portions of water and one 70 ml portion of saturated aqueous sodium chloride solution, and dried over magnesium sulfate to give an oil. The oil is chromatographed on silica gel with dichloromethane to give an oil, which crystallizes to yield 3-(3-fluorophenyl)-1,3-dihydro-1'-phenoxycarbonylspiro[benzo(c)thiophene-1,4'-piperidine], m.p. 134°-142° C. A portion is recrystallized twice from toluene:hexane, m.p. 144°-146° C.

Workup

  1. washThe resultant mixture is washed with two 175 ml portions of 10% aqueous sodium hydroxide solution, two 150 ml portions of water and one 70 ml portion of saturated aqueous sodium chloride solution
  2. dry with materialdried over magnesium sulfate
  3. customto give an oil
  4. customThe oil is chromatographed on silica gel with dichloromethane
  5. customto give an oil, which
  6. customcrystallizes

Sources & evidence

ORD record
ord-1a78b598fd4c4979b5159e292dc6f6b3
Source dataset
uspto-grants-1983_10
Patent number
US04409229

Reaction notes

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