Hydrazine hydrate (1:1) → N,N-Dimethyl-1-[(2R)-morpholin-2-yl]methanamine

HRID 324958Notes

Reaction equation

HRID 324958 reaction equation
C([N:8]1[CH2:13][CH2:12][O:11][C@@H:10]([CH2:14][N:15]([CH3:17])[CH3:16])[CH2:9]1)C1C=CC=CC=1.O.NN>C(O)C.[C].[Pd]>[CH3:16][N:15]([CH2:14][C@@H:10]1[O:11][CH2:12][CH2:13][NH:8][CH2:9]1)[CH3:17]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 53812626HCID 53812626, compound

Product 1

HCID 28362281N,N-Dimethyl-1-[(2R)-morpholin-2-yl]methanamineYield 88.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

(S)-4-Benzyl-2-(N,N-dimethylaminomethyl)morpholine (78.9 g) was dissolved in ethanol (800 ml) and 10% palladium carbon (31.1 g) and hydrazine monohydrate (22.1 g) were added with stirring at room temperature. The mixture was refluxed with stirring for 1 hour. After cooling, the reaction mixture was filtered through celite and the solvent was distilled off to give 42.8 g of (R)-2-(N,N-dimethylaminomethyl)morpholine as a pale-yellow oil.

Workup

  1. temperatureThe mixture was refluxed
  2. stirringwith stirring for 1 hour
  3. temperatureAfter cooling
  4. filtrationthe reaction mixture was filtered through celite
  5. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-0585ed9c2ff640e5b1bc8ba7c7237d7d
Source dataset
uspto-grants-2001_04
Patent number
US06221864B1

Reaction notes

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