Phosgene → HCID 20263008, compound

HRID 464415Notes

Reaction equation

HRID 464415 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]([CH3:24])[CH:19]=2)[CH2:13]1)C1C=CC=CC=1.N1CCCC1>C(Cl)Cl>[CH3:24][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

5

Reactant 3

HCID 6371PhosgeneHCID 31268PyrrolidineHCID 20263013HCID 20263013, compound

Product 1

HCID 20263008HCID 20263008, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 9.5 g (0.097 mole) of phosgene in 100 ml of methylene chloride under nitrogen gas was added dropwise 23.84 g (0.088 mole) of 1-benzyl-3-(3-methylphenoxy)pyrrolidine in 50 ml of methylene chloride. When the addition was complete, thin-layer chromatography showed no starting pyrrolidine remained. The reaction mixture was stirred overnight and concentrated in vacuo to give an oil. The oil was triturated with 30/60 petroleum ether to remove benzyl chloride. A white solid, 14.4 g of crude product was obtained. A portion was recrystallized from hexane.

Workup

  1. additionWhen the addition
  2. concentrationconcentrated in vacuo
  3. customto give an oil
  4. customThe oil was triturated with 30/60 petroleum ether
  5. customto remove benzyl chloride

Sources & evidence

ORD record
ord-34804d82c0e44bd0bc828d2434368db8
Source dataset
uspto-grants-1985_10
Patent number
US04547514

Reaction notes

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