Phosgene → HCID 20263094, compound

HRID 464424Notes

Reaction equation

HRID 464424 reaction equation
[C:1]([Cl:4])(Cl)=[O:2].C([N:12]1[CH2:16][CH2:15][CH:14]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Br:24])[CH:19]=2)[CH2:13]1)C1C=CC=CC=1>C1C=CC=CC=1>[Br:24][C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][CH:21]=1)[O:17][CH:14]1[CH2:15][CH2:16][N:12]([C:1]([Cl:4])=[O:2])[CH2:13]1

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 20263074HCID 20263074, compound

Product 1

HCID 20263094HCID 20263094, compoundYield 188.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent3×

Procedure

To a benzene solution of 5.05 g (0.051 mole) of phosgene in 50 ml of benzene at 10° C. under nitrogen gas was added dropwise 15.5 g (0.047 mole) of 1-benzyl-3-(3-bromophenoxy)pyrrolidine in 50 ml of dry benzene. The reaction mixture was stirred for 6 hr, diluted with ice-water mixture. The benzene layer which developed was separated and dried over magnesium sulfate and concentrated in vacuo to give 27 g of oil. The oil was triturated with hot 30/60 petroleum ether and the mixture stirred overnight. The petroleum layer was decanted and the oil again treated with fresh petroleum ether. The oil was again separated to give 20 g of oil crude product.

Workup

  1. customThe benzene layer which developed was separated
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7cccbfa9f6164509b1d4589be64b2a74
Source dataset
uspto-grants-1985_10
Patent number
US04547514

Reaction notes

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