Phosgene → HCID 13534256, compound

HRID 464417Notes

Reaction equation

HRID 464417 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][C:21]([F:24])=[C:20]([Cl:25])[CH:19]=2)[CH2:13]1)C1C=CC=CC=1>C1C=CC=CC=1>[Cl:25][C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][C:21]=1[F:24])[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 20263038HCID 20263038, compound

Product 1

HCID 13534256HCID 13534256, compoundYield 7.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a stirred solution of 19.6 g (0.2 mole) of phosgene in benzene (100 ml of 2 molar solution) under nitrogen gas was added dropwise 61.1 g (0.2 mole) of 1-benzyl-3-(3-chloro-4-fluorophenoxy)pyrrolidine in 100 ml of dry benzene. The mixture was stirred for about 21/2 days. The mixture was filtered to remove 8 g of starting compound as the hydrochloride salt and the filtrate was concentrated under reduced pressure. The resulting oil was triturated in succession with three 100 ml portions of 30/60 petroleum ether. The oil residue was again subjected to reduced pressure to remove petroleum ether. The oil residue, 46 g contained 5-10% benzyl chloride. The combined ether washes yielded 4 g of crystalline product on standing. Yield of product was 50 g (93%)., m.p. 63°-65° C.

Workup

  1. filtrationThe mixture was filtered
  2. customto remove 8 g of starting compound as the hydrochloride salt
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe resulting oil was triturated in succession with three 100 ml portions of 30/60 petroleum ether
  5. customto remove petroleum ether

Sources & evidence

ORD record
ord-a5c55af80e1d4cf1b20f08a792610890
Source dataset
uspto-grants-1985_10
Patent number
US04547514

Reaction notes

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