Phenyl chloroformate → HCID 12694087, compound

HRID 1248513Notes

Reaction equation

HRID 1248513 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 reaction 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-59625746e60b44bead52f537e47560a6
Source dataset
uspto-grants-1985_06
Patent number
US04524207

Reaction notes

Loading…