Dimethylamine → HCID 68680669, compound

HRID 1830004Notes

Reaction equation

HRID 1830004 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 2

HCID 674DimethylamineHCID 58650607HCID 58650607, compound

Product 1

HCID 68680669HCID 68680669, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of (2S,5S)-2-(chloromethyl)-5-methyl-4-benzylmorpholine (1 equivalent) and dimethylamine (5 equivalents) in ethanol, was heated at 150° C. for 36 hours in a sealed high pressure vessel. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was taken up in 1 N HCl, and the solution was washed with CH2Cl2. The water phase was made basic with a 30% aq. NaOH solution (pH=12) and extracted with CH2Cl2. The organic extracts were collected and dried over Na2SO4. Evaporation of the solvent under reduced pressure afforded (2S,5S)-2-[dimethylamino(methyl)]-5-methyl-4-benzylmorpholine as a yellow oil. GC/MS: 247 (2%, M-H), 204 (55%, M-NMe2), Rt=15.5 min; 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. washthe solution was washed with CH2Cl2
  4. extractionextracted with CH2Cl2
  5. customThe organic extracts were collected
  6. dry with materialdried over Na2SO4
  7. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-82f1bf09cdce4a67baeb3e13d3e83417
Source dataset
uspto-grants-2006_06
Patent number
US07064215B2

Reaction notes

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