4-Methylmorpholine → HCID 18467925, compound

HRID 374966Notes

Reaction equation

HRID 374966 reaction equation
[Cl:1][C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.C[N:14]1CCOCC1.[NH:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1>C1(C)C=CC=CC=1>[C:2]([Cl:1])(=[O:4])[NH2:14].[NH:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 31268PyrrolidineHCID 94429Triphosgene

Product 1

HCID 18467925HCID 18467925, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

A stirring solution of triphosgene (27.78 g, 0.103 mol) in 40 mL toluene was cooled to -20 ° C. in an ice/salt bath under a blanket of nitrogen and treated with a solution of N-methylmorpholine (27.3 g, 0.27 mol) in 20 mL of toluene dropwise over 1 h. This solution was then treated with a solution of pyrrolidine (19.8 g, 0.27 mol) in 30 mL of toluene over a period of 30 m. The solution was allowed to warm to room temperature, filtered and the filtrate concentrated in vacuo to give an oil that was purified by vacuum distillation through a 12" Vigeraux column to give 20.7 g, 56%, bp 58° C. @0.6 mm, of pure product.

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate concentrated in vacuo
  3. customto give an oil that
  4. distillationwas purified by vacuum distillation through a 12" Vigeraux column
  5. customto give 20.7 g, 56%, bp 58° C. @0.6 mm

Sources & evidence

ORD record
ord-3c027af7149c43299d25c96fc0fed44b
Source dataset
uspto-grants-1996_01
Patent number
US05482947

Reaction notes

Loading…