N,N-Diethylethylenediamine → N-(2-diethylaminoethyl)-4-(1,4-dihydroindeno[1,2-c]pyrazol-3-yl)benzamide

HRID 990989Notes

Reaction equation

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

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of methyl 4-(1,4-dihydroindeno[1,2-c]pyrazol-3-yl)benzoate (0.3 g) and N,N-diethylethylenediamine (1 ml) was heated at 150° C. for 3.5 hours and then at 180° C. for 2 hours. The mixture was cooled and dissolved in industrial methylated spirit and this solution was preabsorbed onto silica which was applied to the top of a flash column. The column was eluted with dichloromethane/industrial methylated spirit/triethylamine (25:2:1) to give a solid which was stirred with water for 1 hour, filtered and dried under vacuum at 60° C. to give N-(2-diethylaminoethyl)-4-(1,4-dihydroindeno[1,2-c]pyrazol-3-yl)benzamide, m.p. 172-174° C.

Workup

temperatureThe mixture was cooled
customthis solution was preabsorbed onto silica which
washThe column was eluted with dichloromethane/industrial methylated spirit/triethylamine (25:2:1)
customto give a solid which
filtrationfiltered
customdried under vacuum at 60° C.

Sources & evidence

ORD record: ord-0cc48823cb7140eb956942802c4cf48a
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06462036B1

Reaction notes

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