Water → HCID 10152749, compound

HRID 1836314Notes

Reaction equation

HRID 1836314 reaction equation
[CH3:1][C:2]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][NH:3]1.Cl[CH2:20][C:21]([N:23]([CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[F:40])[CH:24]1[CH2:32][C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:25]1)=[O:22].[C:41](=O)([O-])[O-].[K+].[K+].O>C(#N)C>[CH2:1]([C:2]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][N:3]1[CH2:20][C:21]([N:23]([CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[F:40])[CH:24]1[CH2:32][C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:25]1)=[O:22])[CH3:41]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 22380830HCID 22380830, compoundHCID 22380835HCID 22380835, compound

Product 1

HCID 10152749HCID 10152749, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-Methyl-1-o-tolyl-1,2,3,4-tetrahydro-isoquinoline (96 mg, 0.40 mmol), 2-chloro-N-(2-fluoro-benzyl)-N-indan-2-yl-acetamide (147 mg, 0.40 mmol), and potassium carbonate (111 mg, 0.80 mmol) in actonitrile (10 ml) is heated at reflux for 30 hours. The reaction mixture is cooled, treated with water, and extracted with ethyl acetate. The combined extracts are washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue is purified by preparative thin layer chromatography to give 2-(1-Ethyl-1-o-tolyl-3,4-dihydro-1H-isoquinolin-2-yl)-N-(2-fluoro-benzyl)-N-indan-2-yl-acetamide (Compound 4) as a pale yellow oil. LSMS 519.3 (MH+).

Workup

  1. temperatureis heated
  2. temperatureat reflux for 30 hours
  3. temperatureThe reaction mixture is cooled
  4. extractionextracted with ethyl acetate
  5. washThe combined extracts are washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-81147dc074a64695b04fd714fa919eb6
Source dataset
uspto-grants-2004_08
Patent number
US06777422B2

Reaction notes

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