Benzene → 3-(3-Chlorophenoxy)pyrrolidine-1-carbonyl chloride

HRID 464421Notes

Reaction equation

HRID 464421 reaction equation
C1C=CC=CC=1.[C:7]([Cl:10])(Cl)=[O:8].C([N:18]1[CH2:22][CH2:21][CH:20]([O:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[CH:25]=2)[CH2:19]1)C1C=CC=CC=1>O1CCCC1>[Cl:30][C:26]1[CH:25]=[C:24]([CH:29]=[CH:28][CH:27]=1)[O:23][CH:20]1[CH2:21][CH2:22][N:18]([C:7]([Cl:10])=[O:8])[CH2:19]1

Participants

5

Reactant 3

HCID 241BenzeneHCID 6371PhosgeneHCID 129995671-Benzyl-3-(3-chlorophenoxy)pyrrolidine

Product 1

HCID 129995883-(3-Chlorophenoxy)pyrrolidine-1-carbonyl chlorideYield 8.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A benzene solution of 450 ml of 2M phosgene (0.9 mole) was cooled to 10° C. and while stirring, 210 g (0.81 mole) of 1-benzyl-3-(3-chlorophenoxy)pyrrolidine in 210 ml of tetrahydrofuran was added over a 31/2 hr period. The reaction mixture was allowed to stir overnight and then filtered to remove the hydrochloric acid salt of unreacted starting material. The filtrate was evaporated to give a dark colored oil which was triturated with three 500 ml portions of 30/60 petroleum ether decanting off the petroleum ether each time from the oil residue. The petroleum ether layers were cooled and the oils which separated were combined to give 17 g of pure title product as an oil. After washing with more petroleum ether, the oil (203 g) residue contained about 17% benzyl chloride by NMR analysis. Yield of contained product in both portions was 88%.

Workup

  1. stirringto stir overnight
  2. filtrationfiltered
  3. customto remove the hydrochloric acid salt
  4. customThe filtrate was evaporated
  5. customto give a dark colored oil which
  6. customwas triturated with three 500 ml portions of 30/60 petroleum ether decanting off the petroleum ether each time from the oil residue
  7. temperatureThe petroleum ether layers were cooled
  8. customthe oils which separated

Sources & evidence

ORD record
ord-d47a35646f904805a2691190a96e2c8d
Source dataset
uspto-grants-1985_10
Patent number
US04547514

Reaction notes

Loading…