Phosgene → HCID 20262995, compound

HRID 464425Notes

Reaction equation

HRID 464425 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]=[CH:20][CH:19]=2)[CH2:13]1)C1C=CC=CC=1>C(Cl)Cl>[O:17]([CH:14]1[CH2:15][CH2:16][N:12]([C:1]([Cl:4])=[O:2])[CH2:13]1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 20262996HCID 20262996, compound

Product 1

HCID 20262995HCID 20262995, compoundYield 145.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 9.5 g (0.097 mole) of phosgene in 200 ml of methylene chloride under nitrogen gas was added dropwise with stirring, 30.2 g (0.88 mole) of 1-benzyl-3-phenoxypyrrolidine in 100 ml of methylene chloride over a 45 minute period. The reaction mixture was stirred additionally for 20 minutes. The reaction mixture was concentrated in vacuo to give 31.9 g of oil. The oil was triturated with boiling 30/60 petroleum ether and the mixture was cooled. The ether layer was decanted off and the trituration in petroleum ether procedure was repeated 3 times. The oil contained a trace of benzyl chloride as indicated by thin-layer chromatography.

Workup

  1. stirringThe reaction mixture was stirred additionally for 20 minutes
  2. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-8425c29bda5a4762b112ce06495c29ff
Source dataset
uspto-grants-1985_10
Patent number
US04547514

Reaction notes

Loading…