Phosgene → 3-(3,5-Dichlorophenoxy)-1-pyrrolidinecarbonyl Chloride

HRID 464419Notes

Reaction equation

HRID 464419 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]=[C:22]([Cl:24])[CH:21]=[C:20]([Cl:25])[CH:19]=2)[CH2:13]1)C1C=CC=CC=1>C1C=CC=CC=1>[Cl:24][C:22]1[CH:23]=[C:18]([CH:19]=[C:20]([Cl:25])[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 202629731-Benzyl-3-(3,5-dichlorophenoxy)pyrrolidine

Product 1

HCID 135342583-(3,5-Dichlorophenoxy)-1-pyrrolidinecarbonyl Chloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Conditions

Temperature
5 °C

Procedure

To a stirred solution of 200 ml of 2 molar phosgene in benzene under nitrogen gas was added dropwise over a 3 hr period, a solution of 115 g (0.358 mole) of 1-benzyl-3-(3,5-dichlorophenoxy)pyrrolidine in 100 ml of benzene. The resulting solution was concentrated on a rotary evaporator to give an oil. The oil was triturated three times with boiling 30/60 petroleum ether, decanting each time. The oil residue solidified on cooling. The solid was taken up in benzene and the solution filtered, charcoaled and filtered. Crystalline product was obtained by adding ligroin and cooling to 5° C. in the amount of 92.7 g (87.9%), m.p. 105°-107° C. A purer 3 g sample, m.p. 106°-108° C. was obtained from the petroleum ether on standing.

Workup

  1. concentrationThe resulting solution was concentrated on a rotary evaporator
  2. customto give an oil
  3. customThe oil was triturated three times
  4. customdecanting each time
  5. temperatureon cooling
  6. filtrationthe solution filtered
  7. filtrationfiltered
  8. customCrystalline product was obtained

Sources & evidence

ORD record
ord-263eb2f0571a44b783b4a7c21c91d3c1
Source dataset
uspto-grants-1985_10
Patent number
US04547514

Reaction notes

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