Hydrazine hydrate (1:1) → [3-Cyano-4-(4-phenylpiperidinyl)pyridin-2-yl]-hydrazine

HRID 587628Notes

Reaction equation

Br[C:2]1[C:7]([C:8]#[N:9])=[C:6]([N:10]2[CH2:15][CH2:14][CH:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)[CH:5]=[CH:4][N:3]=1.O.[NH2:23][NH2:24]>C1COCC1>[C:8]([C:7]1[C:2]([NH:23][NH2:24])=[N:3][CH:4]=[CH:5][C:6]=1[N:10]1[CH2:15][CH2:14][CH:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:12][CH2:11]1)#[N:9]

Participants

Conditions

Temperature: 160 °C

Procedure

To a solution of compound D6 (0.5 mg, 1.461 mmol) in THF (4 ml), was added hydrazine monohydrate (0.366 g, 7.305 mmol). The reaction mixture was heated at 160° C. under microwave irradiation for 15 min. After cooling, the resulting mixture was concentrated in vacuo. The residue thus obtained was purified by column chromatography (silica gel; DCM/7M solution of NH3 in MeOH up to 3% as eluent). The desired fractions were collected and concentrated in vacuo to yield intermediate compound D7 (0.380 g, 89%) as a white solid.

Workup

temperatureAfter cooling
concentrationthe resulting mixture was concentrated in vacuo
customThe residue thus obtained
customwas purified by column chromatography (silica gel; DCM/7M solution of NH3 in MeOH up to 3% as eluent)
customThe desired fractions were collected
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-61d3386e87564b4fb106c2749e8365a0
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09226930B2

Reaction notes

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