Acrylamide → 4-(5H-dibenzo[a,d]cyclohepten-5-yl)-1-(2-carbamoylethyl)piperidine
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]([NH2:26])(=[O:25])[CH:23]=[CH2:24].C(N(CC)CC)C.N1CCCCC1>C(O)(C)C>[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](=[O:25])[NH2:26])[CH2:20][CH2:21]3)[C:7]=2[CH:15]=[CH:14][CH:13]=1Participants
Procedure
1.00 gram (3.62 millimoles) of 4-(5H-dibenzo-[a,d]cyclohepten-5-yl)piperidine, 0.26 gram (3.62 millimoles) of acrylamide, 0.04 gram (0.36 millimole) of triethylamine and 20 milliliters of isopropyl alcohol were stirred together at reflux temperature while protected from atmospheric moisture. A TLC analysis of a sample of the reaction mixture indicated presence of some piperidine compound but no acrylamide. 50 milligrams (0.7 millimole) of acrylamide in 1 milliliter of isopropyl alcohol was added and the reaction continued at reflux temperature for a total of about 3.5 hours. The reaction mixture was allowed to cool to room temperature and the solvent then removed in vacuo to obtain the desired 4-(5H-dibenzo[a,d]cyclohepten-5-yl)-1-(2-carbamoylethyl)piperidine product as residue. The crude product was crystallized from methylene chloride/hexane, then dried in vacuo overnight at 100° C. to obtain 900 milligrams (72 percent yield) of product, m.p. 135°-140° C.
Workup
- temperatureat reflux temperature while protected from atmospheric moisture
- temperatureat reflux temperature for a total of about 3.5 hours
- customthe solvent then removed in vacuo
Sources & evidence
- ORD record
- ord-14ae8f8b5cfc4624beb885fa052ddb29
- Source dataset
- uspto-grants-1988_07
- Patent number
- US04758577
Reaction notes
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