Hydrochloric Acid → HCID 14257841, compound

HRID 2231713Notes

Reaction equation

HRID 2231713 reaction equation
[ClH:1].[C:2]1([CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([CH:16]=[O:17])[CH2:12][CH2:11]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1C1(C=O)CCNCC1.BrCCC1C=CC=CC=1.Cl>CN(C=O)C.CO.CCOC(C)=O.O>[ClH:1].[CH3:18][C:19]1[CH:24]=[CH:23][C:22]([C:16]([CH:13]2[CH2:14][CH2:15][N:10]([CH2:9][CH2:8][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:11][CH2:12]2)=[O:17])=[CH:21][CH:20]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7666Phenethyl bromideHCID 19806885HCID 19806885, compoundHCID 86742524HCID 86742524, compound

Product 1

HCID 14257841HCID 14257841, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 21584119Ethylacetate methanolSolvent

Conditions

Temperature
100 °C

Procedure

(4-Methylphenyl)[1-(2-phenylethyl)-4-piperidinyl -methanone HCl. 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 recrystalized 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 recrystalized twice from EtOH/Et2O

Sources & evidence

ORD record
ord-4936d43f8c4641dbbb5c45bd4aa4245a
Source dataset
uspto-grants-1988_11
Patent number
US04783471

Reaction notes

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