Hydrazine hydrate (1:1) → HCID 21332725, compound

HRID 1629971Notes

Reaction equation

HRID 1629971 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11](=O)[CH2:12][CH2:13][N:14](C)C)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].O.[NH2:19]N>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH2:12][CH2:13][NH:14][N:19]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 211864HCID 211864, compound

Product 1

HCID 21332725HCID 21332725, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 1-(3,4-dimethoxyphenyl-3-(dimethylamino)propan-1-one (2.9 g, 0.0122 moles, 1 equiv.) in absolute ethanol was added hydrazine hydrate (99%-100%) (1.18 ml, 0.0244 moles, 2 equiv) drop wise. After that the reaction mixture was refluxed for 4 h at 80° C. under inert atmosphere. Consumption of starting materials was confirmed by LC-MS analysis and TLC. Ethanol and excess hydrazine hydrate was evaporated under reduced pressure and to the crude product was stirred with diethyl ether at RT for 30 mins, filtered washed with ether and finally dried under vacuum to get 2.4 g (95% yield) of the title product as yellow solid.

Workup

  1. customConsumption of starting materials
  2. customEthanol and excess hydrazine hydrate was evaporated under reduced pressure and to the crude product
  3. filtrationfiltered
  4. washwashed with ether
  5. customfinally dried under vacuum

Sources & evidence

ORD record
ord-229cdc57d4a5460b8590adb6594a944a
Source dataset
uspto-grants-2014_07
Patent number
US08791114B2

Reaction notes

Loading…