Phenyl chloroformate → HCID 12694092, compound

HRID 647540Notes

Reaction equation

HRID 647540 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH:18]1[S:32][C:25]2([CH2:30][CH2:29][N:28](C)[CH2:27][CH2:26]2)[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]1=2>ClCCl>[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH:18]1[S:32][C:25]2([CH2:26][CH2:27][N:28]([C:2]([O:4][C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)=[O:3])[CH2:29][CH2:30]2)[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]1=2

Participants

4

Reactant 2

HCID 15891Phenyl chloroformateHCID 12694073HCID 12694073, compound

Product 1

HCID 12694092HCID 12694092, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To 3.83 g of phenyl chloroformate in 850 ml of dichloromethane is added a solution of 6.73 g of the free base 3-(2-chlorophenyl)-1,3-dihydro-1'-methylspiro[benzo(c)thiophene-1,4'-piperidine] of Example 32 in 75 ml of dichloromethane over two minutes. The reaction is stirred at ambient temperature for 64 hours, then diluted with 200 ml of dichloromethane and washed with two 300 ml portions of 5% aqueous sodium hydroxide solution, two 200 ml portions of water and one 75 ml portion of brine. The solution is dried over magnesium sulfate and evaporated to an oil. The oil is chromatographed on a silca gel with dichloromethane to give an oil of 3-(-2-chlorophenyl)-1,3-dihydro-1'-phenoxy carbonylspiro[benzo(c)thiophene-1,4'-piperidine].

Workup

  1. washwashed with two 300 ml portions of 5% aqueous sodium hydroxide solution, two 200 ml portions of water and one 75 ml portion of brine
  2. dry with materialThe solution is dried over magnesium sulfate
  3. customevaporated to an oil
  4. customThe oil is chromatographed on a silca gel with dichloromethane

Sources & evidence

ORD record
ord-30533b27c380449da9d7b731929ee5dc
Source dataset
uspto-grants-1983_10
Patent number
US04409229

Reaction notes

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