Dimethylamine → HCID 59857257, compound

HRID 1170018Notes

Reaction equation

HRID 1170018 reaction equation
Cl[CH2:2][C@H:3]1[O:8][CH2:7][C@@H:6]([CH3:9])[N:5]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:4]1.[CH3:17][NH:18][CH3:19].C(O)C>>[CH3:17][N:18]([CH2:2][C@@H:3]1[O:8][CH2:7][C@@H:6]([CH3:9])[N:5]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:4]1)[CH3:19]

Participants

4

Reactant 3

HCID 674DimethylamineHCID 702EthanolHCID 59857314HCID 59857314, compound

Product 1

HCID 59857257HCID 59857257, compound

Conditions

Temperature
150 °C

Procedure

A mixture of (2S,5R)-2-(chloromethyl)-5-methyl-4-benzylmorpholine (1 equivalent) and dimethylamine in ethanol (33%, approx. 5.6 M, 5 equivalents) was heated at 150° C. over 2 days in a glass pressure vessel. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was dissolved in 1 N HCl, and the solution was washed with CH2Cl2. The water phase was made basic with 30% NaOH solution (to pH=12) and extracted with CH2Cl2. The organic extracts were collected and dried (Na2SO4). Evaporation of the solvent under reduced pressure afforded (2S,5R)-2-[dimethylamino(methyl)]-5-methyl-4-benzylmorpholine as a brown oil which was used in the next step without purification. GC/MS: 247 (2%, M-H), 204 (55%, M-NMe2), Rt 15.5 minutes; LC/MS m/z 249.2 (MH+), Rt 0.72 minutes.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in 1 N HCl
  4. washthe solution was washed with CH2Cl2
  5. extractionextracted with CH2Cl2
  6. customThe organic extracts were collected
  7. dry with materialdried (Na2SO4)
  8. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-2ce91afe315d4e62a5c08b9d8061718e
Source dataset
uspto-grants-2010_11
Patent number
US07825132B2

Reaction notes

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