Acetic Acid → (Z)-ethyl 2-cyano-3-(4-(4-methylpiperazin-1-yl)phenyl)but-2-enoate

HRID 2176914Notes

Reaction equation

[CH3:1][CH2:2][O:3][C:4]([CH2:6][C:7]#[N:8])=[O:5].C([O-])(=O)C.[NH4+].C(O)(=O)C.[CH3:18][N:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:30]=[CH:29][C:28]([C:31](=O)[CH3:32])=[CH:27][CH:26]=2)[CH2:21][CH2:20]1>C1C=CC=CC=1.O>[C:7](/[C:6](=[C:31](/[C:28]1[CH:27]=[CH:26][C:25]([N:22]2[CH2:21][CH2:20][N:19]([CH3:18])[CH2:24][CH2:23]2)=[CH:30][CH:29]=1)\[CH3:32])/[C:4]([O:3][CH2:2][CH3:1])=[O:5])#[N:8]

Participants

Conditions

Temperature: 137.5 °C

Procedure

Ethyl cyano acetate (3.12 g, 27.6 mmol), ammonium acetate (123 mg, 1.76 mmol), acetic acid (0.2 ml, 3.5 mmol) were added successively to a stirred solution of 1-(4-(4-methylpiperazin-1-yl)phenyl)ethanone (5.0 g, 23 mmol) in benzene (25 ml) and stirred for 36 h at 135-140° C. The reaction mixture was poured into water and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the crude product. This was purified by column chromatography using 2% methanol in CHCl3 as eluent to afford (Z)-ethyl 2-cyano-3-(4-(4-methylpiperazin-1-yl)phenyl)but-2-enoate as yellow liquid 2.30 g (32.4%).

Workup

extractionextracted with ethyl acetate
washThe combined organic layer was washed with brine
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customto give the crude product
customThis was purified by column chromatography

Sources & evidence

ORD record: ord-d55d6f5570954d8ea54cf21a1171517d
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067888B2

Reaction notes

Loading…