2,6-Dimethylmorpholine, cis- → HCID 22818569, compound

HRID 1155330Notes

Reaction equation

HRID 1155330 reaction equation
[CH3:1][C@H:2]1[O:7][C@@H:6]([CH3:8])[CH2:5][NH:4][CH2:3]1.[C:9]([C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH:20]([CH3:23])[CH2:21]Br)=[C:15]([Cl:24])[CH:14]=1)([CH3:12])([CH3:11])[CH3:10]>C(#N)C.C(Cl)Cl>[C:9]([C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH:20]([CH3:21])[CH2:23][N:4]2[CH2:5][C@H:6]([CH3:8])[O:7][C@H:2]([CH3:1])[CH2:3]2)=[C:15]([Cl:24])[CH:14]=1)([CH3:12])([CH3:11])[CH3:10]

Participants

5

Reactant 2

HCID 6415002,6-Dimethylmorpholine, cis-HCID 20541578HCID 20541578, compound

Product 1

HCID 22818569HCID 22818569, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 23 g of 2,6-cis-dimethylmorpholine and 30.4 g of 3-(p-tert-butyl-o-chlorophenyl)-2-methylpropyl bromide in 150 ml of acetonitrile is refluxed for 4 hours. The crude product is dissolved in methylene chloride, the solution is washed with water, aqueous sodium bicarbonate solution and again with water, and dried over Na2SO4, the solvent is evaporated and the residue is distilled. There is obtained 22 g of N-[3-(p-tert-butyl-o-chlorophenyl)-2-methylpropyl]-2,6-cis-dimethylmorpholine (active ingredient no. 2); b.p. (0.05 mm) 133°-135° C.

Workup

  1. washthe solution is washed with water, aqueous sodium bicarbonate solution and again with water
  2. dry with materialdried over Na2SO4
  3. customthe solvent is evaporated
  4. distillationthe residue is distilled

Sources & evidence

ORD record
ord-b9e12f3f407a4f669eb4f0471f4ac2c6
Source dataset
uspto-grants-1981_11
Patent number
US04301284

Reaction notes

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