Sodium Iodide → N-Methylaniline

HRID 2248840Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2248840
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[Br:11][CH:12]([OH:14])[CH3:13].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].[CH2:23]([N:27]([CH3:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:24][CH:25]=[CH2:26].FC(F)(F)C(O)=O>CO.O>[C:28]1([N:27]2[CH2:23][CH2:24][CH:12]([OH:14])[CH2:13][CH2:34]2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[CH2:23]([N:27]([CH3:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:24][CH:25]=[CH2:26].[CH3:2][NH:1][C:10]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1.[Br:11][CH2:2][CH2:3][CH:4]=[CH2:5]

Komponenten

12

Edukt 6

HCID 5238Sodium IodideHCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 694601,2,3,4-TetrahydroquinolineHCID 577490Benzenamine, N-3-butenyl-N-methyl-HCID 14202443Ethanol, 1-bromo-

Produkt 4

HCID 7515N-MethylanilineHCID 21241Homoallyl bromideHCID 577490Benzenamine, N-3-butenyl-N-methyl-HCID 27371541-Phenylpiperidin-4-ol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Referring to the above reaction diagram, tetrahydroquinoline may be alkylated in methanol by adding excess bromoethanol, sodium iodide and potassium carbonate and refluxing the solution for 24 hours. The product is preferably isolated in water and purified by vacuum distillation. If phenylpiperazine is the starting material, it is alkylated under the same reaction conditions. A 1-phenyl-4-piperidinol structure is synthesized by preparing N-but-3-enyl--N-methylaniline, and treating with aqueous trifluoroacetic acid. N-but-3-enyl--N-methylaniline is provided by alkylation of N-methylaniline with 4-bromobut-1-ene. 1-Phenyl-3-pyrrolidinol is synthesized by the reaction of aniline with 1,4-dibromo-2-butanol.

Aufarbeitung

  1. temperaturerefluxing the solution for 24 hours
  2. distillationpurified by vacuum distillation
  3. customis alkylated under the same reaction conditions

Quellen und Nachweise

ORD-Eintrag
ord-debd344a8a76421cbf09db4f3ee3f141
Quelldatensatz
uspto-grants-1991_08
Patentnummer
US05041509

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