Phenyl chloroformate → HCID 12694087, compound

HRID 647541Notes

Reaction equation

HRID 647541 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].Br.C[N:13]1[CH2:18][CH2:17][C:16]2([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[CH:20]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([CH3:33])[CH:28]=3)[S:19]2)[CH2:15][CH2:14]1>ClCCl>[CH3:33][C:29]1[CH:28]=[C:27]([CH:20]2[S:19][C:16]3([CH2:17][CH2:18][N:13]([C:2]([O:4][C:5]4[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=4)=[O:3])[CH2:14][CH2:15]3)[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]2=3)[CH:32]=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 15891Phenyl chloroformateHCID 12694065HCID 12694065, compound

Product 1

HCID 12694087HCID 12694087, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To 1.81 g of phenyl chloroformate in 40 ml of dichloromethane is added a solution of 2.98 g of the free base 1,3-dihydro-1'-methyl-3-(3-methylphenyl)spiro[benzo(c)thiophene-1,4'-piperidine] of Example 41 in 35 ml of dichloromethane over 5 minutes. The reaction is stirred at ambient temperature for 21 hours The reactionn is then diluted with 100 ml of dichloromethane; washed with two 150 ml portions of 5% aqueous sodium hydroxide solution, two 100 ml portions of water and one 50 ml portion of brine; and dried over magnesium sulfate to an oil. The oil is chromatographed on silica gel with dichloromethane to yield 1,3-dihydro-3-(3-methylphenyl)-1'-phenoxycarbonylspiro[benzo(c)-thiophene-1,4'-piperidine], m.p. 154°-157° C. A portion is recrystallized from toluene-hexane, m.p. 157°-160° C.

Workup

  1. washwashed with two 150 ml portions of 5% aqueous sodium hydroxide solution, two 100 ml portions of water and one 50 ml portion of brine
  2. dry with materialand dried over magnesium sulfate to an oil
  3. customThe oil is chromatographed on silica gel with dichloromethane

Sources & evidence

ORD record
ord-3de99d0e43ae4e65bbb4fd0cdd732a42
Source dataset
uspto-grants-1983_10
Patent number
US04409229

Reaction notes

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