N,N-Dimethylaniline → HCID 68519385, compound

HRID 2390028Notes

Reaction equation

HRID 2390028 reaction equation
[CH2:1]([CH:8]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C)C1C=CC=CC=1.[Br:27][CH2:28][C:29](Br)=[O:30].O>C(Cl)Cl>[Br:27][CH2:28][C:29]([N:9]1[CH:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10]1)=[O:30]

Participants

6

Reactant 4

HCID 949N,N-DimethylanilineHCID 962WaterHCID 61147Bromoacetyl bromideHCID 20566241HCID 20566241, compound

Product 1

HCID 68519385HCID 68519385, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

89 mg of 3-benzyl-1,2,3,4-tetrahydroisoquinoline obtained in Example 1-d) was dissolved in 2 mL of methylene chloride, and 53 mg of N,N-dimethylaniline, 73 mg of bromoacetylbromide were added thereto, followed by stirring under ice-cooling for 30 minutes. After completion of the reaction, water was added thereto, followed by extraction with chloroform. The chloroform layer was washed with brine and then dried over anhydrous sodium sulfate, and the solvent was removed by evaporation, followed by purification using PLC (hexane:ethyl acetate=1:1) to obtain 120 mg (yield 88%) of 2-(2-bromoacetyl)-3-benzyl-1,2,3,4-tetrahydroisoquinoline as a yellow oily substance. 34 mg of this product was dissolved in 10 mg of aniline, 15 mg of potassium carbonate, and 1 mL of acetonitrile, followed by stirring at 60° C. for 4 hours. After completion of the reaction, the reaction liquid was filtered with ethyl acetate, concentrated under reduced pressure, and purified using PTLC (chloroform:methanol=10:1) to obtain 28 mg (yield 72%) of a title compound as a yellow oily substance.

Workup

  1. temperaturecooling for 30 minutes
  2. additionwas added
  3. extractionfollowed by extraction with chloroform
  4. washThe chloroform layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was removed by evaporation
  7. customfollowed by purification

Sources & evidence

ORD record
ord-2e740c103e2d45729b62f11c877afea7
Source dataset
uspto-grants-2012_09
Patent number
US08273766B2

Reaction notes

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