Reaktionsgleichung
Cl.Cl[CH2:3][CH2:4][N:5]([CH3:9])[CH2:6][CH2:7]Cl.[Cl:10][C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=1)[CH2:14][C:15]#[N:16].[OH-].[Na+]>[Br-].C([P+](CCCC)(CCCC)CCCC)CCCCCCCCCCCCCCC.O>[Cl:10][C:11]1[CH:12]=[C:13]([C:14]2([C:15]#[N:16])[CH2:7][CH2:6][N:5]([CH3:9])[CH2:4][CH2:3]2)[CH:17]=[CH:18][CH:19]=1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
The starting material, 4-(3-chlorophenyl)-1-methylpiperidine-4-carbonitrile was prepared as follows by the procedure of T. Cammack and P. C. Reeves, J. Heterocycl. Chem., 23, 73 (1986): a mixture of 100 g (0.52 mole) of N,N-bis(chloroethyl)methylamine hydrochloride, 80 g (0.53 mole) of 3-chlorobenzyl cyanide, 13 g of hexadecyltributylphosphonium bromide and 750 mL of 50% aqueous sodium hydroxide was stirred at 100° internal temperature for 1 hour. Water (750 mL) was added to the cooled mixture which was then extracted with 500 mL and three 100-mL portions of toluene. Removal of the solvent from the dried solution and rapid short-path distillation of the residue (160° bath temperature, 0.1 mm) gave 107.2 g (88% yield) of 4-(3-chlorophenyl)-1-methylpiperidine-4-carbonitrile as a colorless oil which slowly crystallizes. NMR (CDCl3): δ7.5 (s,1H); 2.3 (m,3H); 3.0 (d,2H); 2.5 (m,2H); 2.4 (s,3H) and 2.1 (m,4H). The hydrochloride had m.p. 235°-236° after crystallization from isopropyl alcohol.
Aufarbeitung
- customThe starting material, 4-(3-chlorophenyl)-1-methylpiperidine-4-carbonitrile was prepared
- extractionwas then extracted with 500 mL and three 100-mL portions of toluene
- customRemoval of the solvent
- distillationfrom the dried solution and rapid short-path distillation of the residue (160° bath temperature, 0.1 mm)
Quellen und Nachweise
- ORD-Eintrag
- ord-66114871ca934f708ca003c175f7e88a
- Quelldatensatz
- uspto-grants-1991_05
- Patentnummer
- US05019650
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