Ethyl Acetate → N-(cyclohexylmethyl)-2-{3-[4-(2-methoxyphenyl)piperazin-1-yl]butanoyl}hydrazinecarboxamide

HRID 1514164Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH:15]([CH3:21])[CH2:16][C:17]([NH:19][NH2:20])=[O:18])[CH2:11][CH2:10]1.[CH2:22]1[CH2:27][CH2:26][CH:25]([CH2:28][N:29]=[C:30]=[O:31])[CH2:24][CH2:23]1.CCOC(C)=O>C1(C)C=CC=CC=1>[CH:25]1([CH2:28][NH:29][C:30]([NH:20][NH:19][C:17](=[O:18])[CH2:16][CH:15]([N:12]2[CH2:11][CH2:10][N:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[O:2][CH3:1])[CH2:14][CH2:13]2)[CH3:21])=[O:31])[CH2:26][CH2:27][CH2:22][CH2:23][CH2:24]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a suspension of 3-[4-(2-methoxyphenyl)piperazin-1-yl]butanohydrazide D12 (0.5 g, 1.71 mmol) in anhydrous toluene (7 mL), cyclohexanemethyl isocyanate (0.25 g, 1.80 mmol) was added dropwise at room temperature, the mixture was heated at 100° C. and stirred for 10 min. The solution was allowed to cool slowly to room temperature, AcOEt (15 mL) was added and the organic phase was washed with water (2×10 mL), dried over MgSO4 and evaporated under reduced pressure to afford 0.909 g N-(cyclohexylmethyl)-2-{3-[4-(2-methoxyphenyl)piperazin-1-yl]butanoyl}hydrazinecarboxamide D13 as an orange oil. The product containing little toluene was used in the next step without further purification.

Workup

temperatureto cool slowly to room temperature
washthe organic phase was washed with water (2×10 mL)
dry with materialdried over MgSO4
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-eb1088f431054907a5c786af232139cd
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222254B2

Reaction notes

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