P-Toluenesulfonylhydrazide → 4-[(4-Cyclopropylcyclohexylamino)methyl]benzoic acid methyl ester

HRID 1633917

Reaction equation

[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][NH:11][CH:12]2[CH2:17][CH2:16][C:15](=[C:18]3[CH2:20][CH2:19]3)[CH2:14][CH2:13]2)=[CH:6][CH:5]=1.C1(C)C=CC(S(NN)(=O)=O)=CC=1>CN(C=O)C.C(OCC)(=O)C.O>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][NH:11][CH:12]2[CH2:17][CH2:16][CH:15]([CH:18]3[CH2:20][CH2:19]3)[CH2:14][CH2:13]2)=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 100 °C

Procedure

4-[(4-Cyclopropylidenecyclohexylamino)methyl]benzoic acid methyl ester (1.1 g, 3.9 mmol) was dissolved in DMF (40 mL) and p-toluenesulfonic acid hydrazide (2.8 g, 15.4 mmol) was added. The reaction was heated to 100° C. for 16 hours. After cooling to room temperature the reaction mixture was diluted with ethyl acetate (75 mL) and water (40 mL) was added. The aqueous phase was extracted with ethyl acetate (25 mL) and the combined organic phases washed with aqueous saturated sodium hydrogen carbonate (2×30 mL) and water (5×30 mL). The organic phase was dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography (25 g silica) using heptane and ethyl acetate (1:1) as eluent to give 4-[(4-cyclopropylcyclohexylamino)methyl]benzoic acid methyl ester.

Workup

temperatureAfter cooling to room temperature the reaction mixture
additionwas added
extractionThe aqueous phase was extracted with ethyl acetate (25 mL)
washthe combined organic phases washed with aqueous saturated sodium hydrogen carbonate (2×30 mL) and water (5×30 mL)
dry with materialThe organic phase was dried (MgSO4)
concentrationconcentrated in vacuo
customThe residue was purified by flash chromatography (25 g silica)

Sources & evidence

ORD record: ord-3d46ad9a739e4d60a06b417c1322a365
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06503949B1

Linked notes

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