Phosgene → HCID 20263004, compound

HRID 464426Notes

Reaction equation

HRID 464426 reaction equation
[C:1]([Cl:4])(Cl)=[O:2].C([N:12]1[CH2:17][CH2:16][CH2:15][CH:14]([O:18][C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=2)[CH2:13]1)C1C=CC=CC=1>C(Cl)Cl>[Cl:26][C:21]1[CH:20]=[C:19]([CH:24]=[CH:23][C:22]=1[Cl:25])[O:18][CH:14]1[CH2:15][CH2:16][CH2:17][N:12]([C:1]([Cl:4])=[O:2])[CH2:13]1

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 20263045HCID 20263045, compound

Product 1

HCID 20263004HCID 20263004, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 8 g (0.085 mole) of phosgene in 100 ml of methylene chloride at 5° C. under nitrogen gas was added slowly a solution of 27.1 g (0.081 mole) of 1-benzyl-3-(3,4-dichlorophenoxy)piperidine in 50 ml of methylene chloride. The reaction mixture was allowed to warm to room temperature over a 2 hr period and then concentrated to a light oil. The oil was triturated with hexane. Starting material, 1.6 g as fine white precipitate, was separated by filtration. The oil was triturated four more times with hexane to remove benzyl chloride. The remaining oil was taken up in 200 ml of benzene and 50 ml of pyridine was added. The mixture was allowed to stir overnight. Some quaternary benzyl chloride salt precipitated and was discarded. The title compound in solution was used in Example 12.

Workup

  1. concentrationconcentrated to a light oil
  2. customThe oil was triturated with hexane
  3. customStarting material, 1.6 g as fine white precipitate, was separated by filtration
  4. customThe oil was triturated four more times with hexane
  5. customto remove benzyl chloride
  6. addition50 ml of pyridine was added
  7. customSome quaternary benzyl chloride salt precipitated

Sources & evidence

ORD record
ord-ecab50b9d914411fa9ac6bbd33ac9c4b
Source dataset
uspto-grants-1985_10
Patent number
US04547514

Reaction notes

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