Phosgene → HCID 20263039, compound

HRID 464427Notes

Reaction equation

HRID 464427 reaction equation
[C:1]([Cl:4])(Cl)=[O:2].C([N:12]1[CH2:17][CH2:16][CH:15]([O:18][C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=2)[CH2:14][CH2:13]1)C1C=CC=CC=1>C(Cl)Cl>[Cl:26][C:21]1[CH:20]=[C:19]([CH:24]=[CH:23][C:22]=1[Cl:25])[O:18][CH:15]1[CH2:16][CH2:17][N:12]([C:1]([Cl:4])=[O:2])[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 20263006HCID 20263006, compound

Product 1

HCID 20263039HCID 20263039, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 16 g (0.16 mole) of phosgene in 200 ml of methylene chloride at 15° C. under nitrogen gas was added dropwise a solution of 47.2 g (0.14 mole) of 1-benzyl-4-(3,4-dichlorophenoxy)piperidine in 100 ml of methylene chloride. The addition was complete within 1 hr and stirring was continued for an additional hour. The mixture was concentrated on a rotary evaporator to give a light oil. The oil was dissolved in isopropyl either and the mixture filtered to remove a small amount of insoluble material. The filtrate was washed with 50 ml of water, dried over magnesium sulfate, filtered and concentrated in vacuo to an oil. The oil was triturated four times with 100 ml of hexane decanting off the hexane each time after cooling. The oil residue, 37 g (86%), was treated with 10 ml of triethylamine to quaternize (precipitate) any excess benzyl chloride.

Workup

  1. additionThe addition
  2. waitwas continued for an additional hour
  3. concentrationThe mixture was concentrated on a rotary evaporator
  4. customto give a light oil
  5. dissolutionThe oil was dissolved in isopropyl either
  6. filtrationthe mixture filtered
  7. customto remove a small amount of insoluble material
  8. washThe filtrate was washed with 50 ml of water
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo to an oil
  12. customThe oil was triturated four times with 100 ml of hexane decanting off the hexane each time
  13. temperatureafter cooling
  14. additionThe oil residue, 37 g (86%), was treated with 10 ml of triethylamine

Sources & evidence

ORD record
ord-f1a12e5356b04cb99033367ecd7f1fa7
Source dataset
uspto-grants-1985_10
Patent number
US04547514

Reaction notes

Loading…