Sodium Iodide → N-Methylaniline

HRID 2248840노트

반응식

HRID 2248840 반응식
[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]

참가 물질

12

반응물 6

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

생성물 4

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-debd344a8a76421cbf09db4f3ee3f141
출처 데이터셋
uspto-grants-1991_08
특허 번호
US05041509

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