4-chloro-N-methylpiperidine → 4-(5H-dibenzo[a,d]cyclohepten-5-yl)-1-methylpiperidine

HRID 1248848Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1248848
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5](Cl)[CH2:4][CH2:3]1.[Mg].Cl[CH:11]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[CH:15]=[CH:14][C:13]2[CH:22]=[CH:23][CH:24]=[CH:25][C:12]1=2>O1CCCC1.C1C=CC=CC=1.O>[CH:22]1[C:13]2[CH:14]=[CH:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[CH:11]([CH:5]3[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]3)[C:12]=2[CH:25]=[CH:24][CH:23]=1

Komponenten

7

Edukt 3

HCID 793424-chloro-N-methylpiperidineHCID 5462224MagnesiumHCID 110751355-Chloro-5H-dibenzo[a,d][7]annulene

Produkt 1

HCID 134042494-(5H-dibenzo[a,d]cyclohepten-5-yl)-1-methylpiperidine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 241BenzeneLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A Grignard solution prepared from 13.4 grams (0.1 mole) of 1-methyl-4-chloropiperidine, 2.43 grams (0.1 gram atom) of magnesium and 100 milliliters of tetrahydrofuran is added dropwise with stirring to a cooled solution of 17.0 grams (0.075 mole) of 5-chloro-5H-dibenzo[a,d]cycloheptene in 100 milliliters of tetrahydrofuran. After completion of the addition, stirring is continued for several hours at ambient temperature. The solvent is then vaporized under reduced pressure to obtain a residue which is dissolved in a biphasic mixture of benzene and water. The benzene solution is washed, dried filtered and the solvent vaporized as previously described to obtain the desired 4-(5H-dibenzo[a,d]cyclohepten-5-yl)-1-methylpiperidine, equational isomer as residue.

Aufarbeitung

  1. additionis added dropwise
  2. additionAfter completion of the addition
  3. waitis continued for several hours at ambient temperature
  4. customto obtain a residue which
  5. washThe benzene solution is washed
  6. customdried
  7. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-671034f57367476ca88f8d3c4744fa1f
Quelldatensatz
uspto-grants-1986_12
Patentnummer
US04626542

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