Water → HCID 10152749, compound

HRID 895691Notes

Reaction equation

HRID 895691 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-bc8780245d7a4e789a50a4fb22832f21
Source dataset
uspto-grants-2005_07
Patent number
US06916830B2

Reaction notes

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