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

HRID 38854Notes

Reaction equation

HRID 38854 reaction equation
C[O:2][C:3](=O)[CH2:4][N:5]1[CH2:10][C@H:9]([CH3:11])[O:8][C@H:7]([CH3:12])[CH2:6]1.O.[NH2:15][NH2:16]>CO>[CH3:12][C@H:7]1[O:8][C@@H:9]([CH3:11])[CH2:10][N:5]([CH2:4][C:3]([NH:15][NH2:16])=[O:2])[CH2:6]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-ccfbeab2e7c64554a6c1d4fb094ce8ee
Source dataset
uspto-grants-2013_09
Patent number
US08524751B2

Reaction notes

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