Water → (1-Benzylpiperidin-4-yl)(2-methylphenyl)methanone

HRID 66674

Reaction equation

HRID 66674 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH3:9].[C:10]1([CH2:16][N:17]2[CH2:22][CH2:21][CH:20]([C:23]#N)[CH2:19][CH2:18]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Cl-].[NH4+].[OH2:27]>O(CC)CC>[CH3:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[C:23]([CH:20]1[CH2:21][CH2:22][N:17]([CH2:16][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:18][CH2:19]1)=[O:27]

Participants

7

Reactant 5

HCID 962WaterHCID 72362-BromotolueneHCID 25517Ammonium ChlorideHCID 7933831-Benzylpiperidine-4-carbonitrileHCID 5462224Magnesium

Product 1

HCID 20530712(1-Benzylpiperidin-4-yl)(2-methylphenyl)methanone

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
10 °C

Procedure

To 7 parts of magnesium is added dropwise a solution of 50 parts of 1-bromo-2-methylbenzene in 140 parts of 1,1'-oxybisethane so that the mixture is refluxing. The whole is stirred for 15 minutes at reflux. The Grignard-complex is cooled to 10° C. and there is added dropwise a solution of 30 parts of 1-(phenylmethyl)-4-piperidinecarbonitrile in 70 parts of 1,1'-oxybisethane. Upon completion, stirring is continued for 4 hours at room temperature. The reaction mixture is decomposed with a solution of 40 parts of ammonium chloride in 400 parts of water. The organic phase is separated, dried, filtered and evaporated, yielding 31 parts of (2-methylphenyl) [1-(phenylmethyl)-4-piperidinyl]methanone as an oily residue.

Workup

  1. temperatureis refluxing
  2. temperatureat reflux
  3. stirringUpon completion, stirring
  4. waitis continued for 4 hours at room temperature
  5. customThe organic phase is separated
  6. customdried
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-2a182cd9dc59402fa13c0b3dd2aec3dc
Source dataset
uspto-grants-1982_08
Patent number
US04342870

Linked notes

Loading…