Hydrazine hydrate (1:1) → 2-[(2R,6S)-2,6-Dimethyl-4-morpholinyl]acetohydrazide

HRID 520548Notes

Reaction equation

HRID 520548 reaction equation
[CH3:1][C@H:2]1[O:7][C@@H:6]([CH3:8])[CH2:5][N:4]([CH2:9][C:10]([O:12]C)=O)[CH2:3]1.O.[NH2:15][NH2:16]>CO>[CH3:1][C@H:2]1[O:7][C@@H:6]([CH3:8])[CH2:5][N:4]([CH2:9][C:10]([NH:15][NH2:16])=[O:12])[CH2:3]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 25985806HCID 25985806, compound

Product 1

HCID 304034132-[(2R,6S)-2,6-Dimethyl-4-morpholinyl]acetohydrazideYield 66.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

Methyl [(2R,6S)-2,6-dimethyl-4-morpholinyl]acetate (5.05 g, 27.0 mmol, see Journal of Fluorine Chemistry (1998) 193-201 for literature preparation) was dissolved in methanol (20 ml) and hydrazine hydrate (2.013 ml, 27.0 mmol) added. The reaction mixture was heated to 70° C. for 18 h. The solvent was partially concentrated in vacuo to remove the methanol and extracted with ethyl acetate (3×20 ml). The combined organic layers were dried and concentrated to afford the title compound as a yellow solid (3.35 g).

Workup

  1. concentrationThe solvent was partially concentrated in vacuo
  2. customto remove the methanol
  3. extractionextracted with ethyl acetate (3×20 ml)
  4. customThe combined organic layers were dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-62e171210a264b969368e921b7d8705d
Source dataset
uspto-grants-2016_05
Patent number
US09326987B2

Reaction notes

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