Hydrazine hydrate (1:1) → HCID 67384438, compound

HRID 1471895Notes

Reaction equation

C[N:2](C)[CH:3]=[C:4]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:5](=O)[CH2:6][CH3:7].O.[NH2:17]N>CCO>[CH2:6]([C:5]1[NH:17][N:2]=[CH:3][C:4]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:7]

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of 1-(dimethylamino)-2-phenylpent-1-en-3-one (3.32 g, 16.33 mmol) in EtOH (80.0 mL) was added hydrazine hydrate (1.58 mL, 32.66 mmol). The resulting mixture was stirred at 80° C. for 3 h. The reaction mixture was cooled to room temperature and concentrated to give a solid. The solid was re-crystallized, using 20% ethanol in water to give the title compound as a white solid (2.81 g). LCMS m/z=173 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 1.31 (t, J=7.58 Hz, 3H), 2.88 (q, J=7.58 Hz, 2H), 7.22-7.30 (m, 1H), 7.35-7.42 (m, 4H).

Workup

temperatureThe reaction mixture was cooled to room temperature
concentrationconcentrated
customto give a solid
customThe solid was re-crystallized

Sources & evidence

ORD record: ord-5337a54f11044afeaf2be1286cc64d43
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09012478B2

Reaction notes

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