Sodium Iodide → N-Methylaniline

HRID 2248840Notes

Reaction equation

HRID 2248840 reaction equation
[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]

Participants

12

Reactant 6

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

Product 4

HCID 7515N-MethylanilineHCID 21241Homoallyl bromideHCID 577490HCID 577490, compoundHCID 27371541-phenylpiperidin-4-ol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-debd344a8a76421cbf09db4f3ee3f141
Source dataset
uspto-grants-1991_08
Patent number
US05041509

Reaction notes

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