Hydrochloric Acid → HCID 14257849, compound

HRID 1165860Notes

Reaction equation

HRID 1165860 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-c19afd1e50434f75b3b502e7adfdc0a8
Source dataset
uspto-grants-1990_03
Patent number
US04912117

Reaction notes

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