Hydrazine → 5-(4-(4-Cyanophenyl)piperidine-1-carbonyl)-4-ethyl-2-methylbenzohydrazide

HRID 541342Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([C:17]3[C:18]([CH2:28][CH3:29])=[CH:19][C:20]([CH3:27])=[C:21]([CH:26]=3)[C:22]([O:24]C)=O)=[O:16])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#[N:2].[NH2:30][NH2:31]>C(O)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[CH2:10][CH2:11][N:12]([C:15]([C:17]3[C:18]([CH2:28][CH3:29])=[CH:19][C:20]([CH3:27])=[C:21]([CH:26]=3)[C:22]([NH:30][NH2:31])=[O:24])=[O:16])[CH2:13][CH2:14]2)=[CH:7][CH:8]=1)#[N:2]

Participants

Conditions

Temperature: 80 °C

Procedure

To a round-bottom flask was added a solution of methyl 5-(4-(4-cyanophenyl)piperidine-1-carbonyl)-4-ethyl-2-methylbenzoate (compound 211.7, 500 mg, 1.28 mmol, 1.00 equiv) in ethanol (20 mL). Hydrazine (4 mL) was added to the reaction mixture. The resulting solution was stirred for 15 h at 80° C., then concentrated in vacuo. The residue was partitioned between water and ethyl acetate. The aqueous layer was extracted with ethyl acetate (2×). The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo to yield 400 mg (80%) of 5-(4-(4-cyanophenyl)piperidine-1-carbonyl)-4-ethyl-2-methylbenzohydrazide as a light yellow solid.

Workup

concentrationconcentrated in vacuo
customThe residue was partitioned between water and ethyl acetate
extractionThe aqueous layer was extracted with ethyl acetate (2×)
dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-28eca4739d034629aea4fd1feea0b09d
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871790B2

Reaction notes

Loading…