Hydrazine hydrate (1:1) → HCID 67384919, compound

HRID 1471899Notes

Reaction equation

HRID 1471899 reaction equation
C[N:2](C)[CH:3]=[C:4]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:5](=O)[CH2:6][CH2:7][CH3:8].O.[NH2:18]N>C(O)C>[C:10]1([C:4]2[CH:3]=[N:2][NH:18][C:5]=2[CH2:6][CH2:7][CH3:8])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67384334HCID 67384334, compound

Product 1

HCID 67384919HCID 67384919, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1-(dimethylamino)-2-phenylhex-1-en-3-one (3.51 g, 16.2 mmol) in ethanol (80.0 mL), was added hydrazine hydrate (1.57 mL, 32.4 mmol). The reaction mixture was stirred at 80° C. After 3 h, the reaction mixture was cooled to room temperature, concentrated under reduced pressure and crystallized in 20% ethanol/H2O to give the title compound as a white solid (3.01 g). LCMS m/z=187.1 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 0.92-1.00 (m, 3H), 1.64-1.76 (m, 2H), 2.75-2.84 (m, 2H), 7.36-7.41 (m, 5H), 7.65 (s, 1H).

Workup

  1. temperaturethe reaction mixture was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. customcrystallized in 20% ethanol/H2O

Sources & evidence

ORD record
ord-3b86add4fc8d45a1b4863279f921f2af
Source dataset
uspto-grants-2015_04
Patent number
US09012478B2

Reaction notes

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