Potassium Carbonate → HCID 22380848, compound

HRID 1836321Notes

Reaction equation

HRID 1836321 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][NH:4][CH:3]1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH3:14].C[CH:16]1[CH2:21][CH2:20][CH2:19]N[CH:17]1[CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH:23]1[CH3:28].ClCC(N([CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=1[F:50])C1CC2C(=CC=CC=2)C1)=O.C(=O)([O-])[O-:52].[K+].[K+]>C(#N)C.O>[F:50][C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][C:44]=1[CH2:43][CH:21]([CH:16]1[CH2:17][C:22]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:28]1)[C:20](=[O:52])[CH2:19][N:4]1[CH2:5][CH2:6][CH2:7][CH:2]([CH3:1])[CH:3]1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH3:14]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 22380835HCID 22380835, compoundHCID 22380846HCID 22380846, compoundHCID 22380854HCID 22380854, compound

Product 1

HCID 22380848HCID 22380848, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-methyl-2-o-tolyl-piperidine and 3-methyl-2-(2-methyl-cyclohexyl)-piperidine (330 mg), 2-chloro-N-(2-fluoro-benzyl)-N-indan-2-yl-acetamide (600 mg), and potassium carbonate (520 mg) in acetonitrile (10 ml) is heated at reflux for 16 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 flash chromatography over silica gel (elution with 5% MeOH/CH2Cl2) to give 4-(2-fluoro-phenyl)-3-indan-2-yl-1-(3-methyl-2-o-tolyl-piperidin-1-yl)-butan-2-one (Compound 10) as a pale yellow oil. LCMS 471.3(MH+).

Workup

  1. temperatureis heated
  2. temperatureat reflux for 16 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 flash chromatography over silica gel (elution with 5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-6dba054b64a74ab3966b1cf308326438
Source dataset
uspto-grants-2004_08
Patent number
US06777422B2

Reaction notes

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