Hydrochloric Acid → HCID 14257849, compound

HRID 1493189Notes

Reaction equation

HRID 1493189 reaction equation
[C:1]1([C:7]([CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C([O-])([O-])=O.[K+].[K+].[ClH:31]>C1(C)C=CC=CC=1.C1(C)C=CC=CC=1.CCOC(C)=O.CO.CCOC(C)=O>[ClH:31].[C:1]1([C:7]([CH:9]2[CH2:14][CH2:13][N:12]([CH2:16][CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:11][CH2:10]2)=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 12503(3-Bromopropyl)benzeneHCID 226102Phenyl(piperidin-4-yl)methanone

Product 1

HCID 14257849HCID 14257849, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 21584019Toluene ethylacetateSolventHCID 21584119Ethylacetate methanolSolvent

Procedure

A solution of phenyl (4-piperidinyl)methanone (18.1 g, 0.096 mol) was dissolved in toluene (200 ml) containing 1-bromo-3-phenylpropane (21.9 g, 0.11 mol, 16.7 ml), K2CO3 (30.4 g, 0.22 mol) and KI (0.2 g) and was refluxed for 64 h. The reaction mixture was filtered and concentrated to give a light yellow oil. This material was dissolved in toluene/EtOAc (1:1) and treated with HCl (0.096 mol) dissolved in CH3OH/EtOAc (2:5, 35 ml) to give a precipitate which was filtered off and recrystallized twice from EtOH/Et2O (150 ml) to give phenyl[1-(3-phenylpropyl)-4-piperidinyl]-methanone hydrochloride, mp 199°-200° C.

Workup

  1. temperaturewas refluxed for 64 h
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated
  4. customto give a light yellow oil
  5. customto give a precipitate which
  6. filtrationwas filtered off
  7. customrecrystallized twice from EtOH/Et2O (150 ml)

Sources & evidence

ORD record
ord-b51e106ed87b4f55bfcc5349090de58a
Source dataset
uspto-grants-1991_06
Patent number
US05021428

Reaction notes

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