Water → HCID 24852801, compound

HRID 551785Notes

Reaction equation

HRID 551785 reaction equation
[C:1]1([CH2:7][C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl[CH2:13][CH2:14][N:15]([CH2:28][CH2:29]Cl)[C:16]([N:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:21][CH2:20][CH2:19]1)=[O:17].O>O1CCCC1.C(OCC)(=O)C>[N:18]1([C:16]([N:15]2[CH2:28][CH2:29][C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)([C:8]#[N:9])[CH2:13][CH2:14]2)=[O:17])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:21][CH2:20][CH2:19]1

Participants

7

Reactant 4

HCID 962WaterHCID 8794PhenylacetonitrileHCID 24758Sodium hydrideHCID 67187631HCID 67187631, compound

Product 1

HCID 24852801HCID 24852801, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.29 ml of phenylacetonitrile in 6 ml of tetrahydrofuran is introduced into a 25 ml three-necked flask. 0.38 g of sodium hydride is subsequently added at 0° C. The reaction medium is stirred at ambient temperature for 30 min and then, at 0° C., 0.5 g of N,N-bis(2-chloroethyl)-3,4-dihydroquinoline-1(2H)-carboxamide is added. The reaction mixture is brought to reflux for 3 h and then ice, water and ethyl acetate are added. The aqueous phase is extracted with ethyl acetate and then the organic phases are combined, washed with water and dried over sodium sulfate and then the solvent is evaporated under reduced pressure. The residue is chromatographed on silica gel with a heptane/methanol gradient from 1/0 to 95/5. 2.91 g of 1-(3,4-dihydroquinolin-1(2H)-ylcarbonyl)-4-phenylpiperidine-4-carbonitrile are obtained.

Workup

  1. temperatureto reflux for 3 h
  2. extractionThe aqueous phase is extracted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. customthe solvent is evaporated under reduced pressure
  6. customThe residue is chromatographed on silica gel with a heptane/methanol gradient from 1/0 to 95/5

Sources & evidence

ORD record
ord-c334be41954946e2ac97d255b8daf67a
Source dataset
uspto-grants-2011_05
Patent number
US07947834B2

Reaction notes

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