Hydrochloric Acid → HCID 14257841, compound

HRID 1165861Notes

Reaction equation

HRID 1165861 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1(C=O)[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.Br[CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[OH2:25].[ClH:26].[CH3:27]N(C=O)C>CO.CCOC(C)=O>[ClH:26].[CH3:27][C:5]1[CH:4]=[CH:1][C:2]([C:3]([CH:8]2[CH2:9][CH2:10][N:11]([CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:12][CH2:13]2)=[O:25])=[CH:7][CH:6]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 6228DimethylformamideHCID 7666Phenethyl bromideHCID 19806885HCID 19806885, compound

Product 1

HCID 14257841HCID 14257841, compound

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture containing 4-(methylphenyl)(4-piperidinyl)methanone (10.5 g, 0.052 mol), 2-bromoethyl benzene (11.1 g, 0.06 mol, 8.2 ml) in dry DMF (125 ml) was stirred at 100° C. for 23 h. The cooled reaction mixture was poured into H2O (600 ml) and extracted with toluene (4×200 ml). The extracts were washed with H2O (2×100 ml) saturated aqueous NaCl (100 ml) and dried over MgSO4. The mixture was filtered and the filtrate concentrated to a solid residue which was dissolved in dry Et2O and filtered. The filtrate was treated with a solution of HCl (0.052 mol) in CH3OH/EtOAc (9:20, 29 ml). The mixture was cooled and filtered to give a light tan powder. The solid was recrystallized twice from EtOH/Et2O to give (4-methylphenyl)[1-(2-phenylethyl)-4-piperidinyl)-methanone hydrochloride, which contains 0.4 mol of water of hydration and melts at 261°-263° C.

Workup

  1. customThe cooled reaction mixture
  2. extractionextracted with toluene (4×200 ml)
  3. washThe extracts were washed with H2O (2×100 ml) saturated aqueous NaCl (100 ml)
  4. dry with materialdried over MgSO4
  5. filtrationThe mixture was filtered
  6. concentrationthe filtrate concentrated to a solid residue which
  7. dissolutionwas dissolved in dry Et2O
  8. filtrationfiltered
  9. temperatureThe mixture was cooled
  10. filtrationfiltered
  11. customto give a light tan powder
  12. customThe solid was recrystallized twice from EtOH/Et2O

Sources & evidence

ORD record
ord-bed9a87b24ed459f863b038f88682678
Source dataset
uspto-grants-1990_03
Patent number
US04912117

Reaction notes

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