3-Acetylbenzonitrile → HCID 10521779, compound

HRID 865936Notes

Reaction equation

HRID 865936 reaction equation
[CH3:1][CH:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)[CH3:3].[C:17]([C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[C:23]#[N:24])(=O)[CH3:18].[BH4-].[Na+]>CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].CO>[CH3:3][CH:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:12][CH2:13][N:14]([CH:17]([C:20]2[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=2)[C:23]#[N:24])[CH3:18])[CH2:15][CH2:16]1)[CH3:1]

Participants

6

Reactant 3

HCID 802223-AcetylbenzonitrileHCID 4311764Sodium borohydrideHCID 109440161-[2-(Propan-2-yloxy)phenyl]piperazine

Product 1

HCID 10521779HCID 10521779, compoundYield 13.5%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1-[2-(methylethoxy)phenyl]piperazine (IPP, 7.28 g, 0.033 mol), 3-acetylbenzonitrile (4.80 g, 0.033 mol), and titanium isopropoxide (11.74 g, 0.041 mol) was stirred at room temperature for 2 h, heated to 80° C. for several minutes, and then cooled to room temperature. Methanol (150 mL) was added and the mixture was heated to dissolve most of the solids. After cooling to room temperature, sodium borohydride (2.27 g, 0.060 mol) was added in portions and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated on a rotary evaporator and the residue was partitioned between 3N NaOH/CH2Cl2. The organic layer was separated, dried (K2CO3), filtered, and evaporated to an oily residue which was passed through flash grade silica using 4:1 hexane:EtOAc as eluant to give 3-[1-[4-[2-(1-methylethoxy)phenyl]-1-piperazinyl]ethyl]benzonitrile as an oil (1.55 g, 13.5%).

Workup

  1. temperatureheated to 80° C. for several minutes
  2. temperaturecooled to room temperature
  3. temperaturethe mixture was heated
  4. dissolutionto dissolve most of the solids
  5. temperatureAfter cooling to room temperature
  6. stirringthe mixture was stirred overnight at room temperature
  7. concentrationThe reaction mixture was concentrated on a rotary evaporator
  8. customthe residue was partitioned between 3N NaOH/CH2Cl2
  9. customThe organic layer was separated
  10. dry with materialdried (K2CO3)
  11. filtrationfiltered
  12. customevaporated to an oily residue which

Sources & evidence

ORD record
ord-377eefd82ac446c19229c87403c1f00a
Source dataset
uspto-grants-1996_10
Patent number
US05569659

Reaction notes

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