Methanol → 1-(4-Chlorophenyl)-1-(2-(piperidin-1-yl)ethyl)hydrazine

HRID 1775944Notes

Reaction equation

Cl[CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.Cl.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][NH2:19])=[CH:14][CH:13]=1.CO>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.[OH-].[Na+].O.C(Cl)(Cl)Cl>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]([CH2:2][CH2:3][N:4]2[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]2)[NH2:19])=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 80 °C

Procedure

1-(2-Chloro-ethyl)piperidine (5 g, 27.9 mmol) was added to a vigorously stirred mixture of 4-chlorophenyl hydrazine hydrochloride (5 g, 27.9 mmol) and tetra-n-butylammonium chloride (0.40 g) in 50% aqueous sodium hydroxide (30 mL). The reaction was heated to 80° C. (oil bath temperature) for 3.5 h. The reaction was cooled, diluted with water and extracted with chloroform. The organic layer was washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure to give a red oil. The oil was subjected to column chromatography (silica gel, eluent: 10% methanol in chloroform) to give a red oil (˜3 g). This was purified again by column chromatography (silica gel, eluent: {tilde over (5)}10% methanol in chloroform) to give a red oil (1.77 g, 25%).

Workup

temperatureThe reaction was cooled
extractionextracted with chloroform
washThe organic layer was washed with brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated under reduced pressure
customto give a red oil

Sources & evidence

ORD record: ord-e9fd7d03411345adb3a0557c203759b6
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260429B2

Reaction notes

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