Phosgene → HCID 13534255, compound

HRID 464416Notes

Reaction equation

HRID 464416 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][C:19]=2[O:24][CH3:25])[CH2:13]1)C1C=CC=CC=1>C1C=CC=CC=1>[CH3:25][O:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=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 20263107HCID 20263107, compound

Product 1

HCID 13534255HCID 13534255, compoundYield 76.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a stirred solution of 60 ml of 2 molar phosgene (0.11 mole) in benzene under nitrogen gas was added dropwise a solution of 29.3 g (0.1 mole) of 1-benzyl-3-(2-methoxyphenoxy)pyrrolidine in 100 ml of benzene. The reaction mixture was stirred at ambient temperature for 2 hours and then concentrated in vacuo to give an oil. The oil was triturated with warm 30/60 petroleum ether and the petroleum ether was decanted to remove benzyl chloride. On the third trituration the oil solidified to give 19.65 g of crude product. The combined petroleum ether decantate, on cooling, yielded an additional 4.8 g, m.p. 80°-81° C. The combined yield was 23.45 g (91.7%). Recrystallization of a 1.25 g sample from 25 ml of 30/60 petroleum ether gave fine white crystals, m.p. 80.5°-82° C. The yield of purified product based on this aliquot was 22.6 g (88%).

Workup

  1. concentrationconcentrated in vacuo
  2. customto give an oil
  3. customThe oil was triturated
  4. temperaturewith warm 30/60 petroleum ether
  5. customthe petroleum ether was decanted
  6. customto remove benzyl chloride

Sources & evidence

ORD record
ord-60b9a30144994a27bf1ecc7e4e5fbe23
Source dataset
uspto-grants-1985_10
Patent number
US04547514

Reaction notes

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