Acrylonitrile → HCID 14253322, compound
Reaction equation
[CH:1]1[C:11]2[CH:10]=[CH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[CH:6]([CH:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:22](#[N:25])[CH:23]=[CH2:24]>C1C=CC=CC=1>[CH:12]1[C:8]2[CH:9]=[CH:10][C:11]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=3[CH:6]([CH:16]3[CH2:17][CH2:18][N:19]([CH2:24][CH2:23][C:22]#[N:25])[CH2:20][CH2:21]3)[C:7]=2[CH:15]=[CH:14][CH:13]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 1.00 gram (3.62 millimoles) of 4-(5H-dibenzo[a,d]cyclohepten-5-yl)piperidine in 20 milliliters of benzene and 0.38 gram (7.24 millimoles) of acrylonitrile were heated at reflux temperature while progress of the reaction was monitored by TLC. After 2.5 hours, the reaction mixture was cooled to room temperature, and the mixture subjected to reduced pressure to vaporize the benzene solvent and excess acrylonitrile and to obtain a solid residue. The solid was recrystallized from acetonitrile/ethyl acetate to obtain a purified 4-(5H-dibenzo[a,d]cyclohepten-5-yl)-1-(2-cyanoethyl)piperidine product which after drying at 100° C. at 1 millimeter mercury pressure for 2 hours and at room temperature for 15 hours, melted at 165°-168° C. The yield of the product was 760 milligrams (64 percent). A second crop was obtained which after recrystallization from acetonitrile was in the form of white needles, m.p. 169°-170° C. The product had elemental analyses as follows:
Workup
- temperatureat reflux temperature while progress of the reaction
- customto obtain a solid residue
- customThe solid was recrystallized from acetonitrile/ethyl acetate
Sources & evidence
- ORD record
- ord-1a81e456196b44269748217c92728909
- Source dataset
- uspto-grants-1988_07
- Patent number
- US04758577
Reaction notes
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