Acetic Acid → 4-(3-Phenoxypropyl]piperazinyl-1-phenylcyclohexanecarbonitrile

HRID 1491651Notes

Reaction equation

HRID 1491651 reaction equation
[C:1]([C:3]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1)#[N:2].[O:16]([CH2:23][CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(O)(=O)C.C([BH3-])#N.[Na+]>C(O)C.O>[O:16]([CH2:23][CH2:24][CH2:25][N:26]1[CH2:27][CH2:28][N:29]([CH:4]2[CH2:5][CH2:6][CH2:7][CH2:8][C:3]2([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:1]#[N:2])[CH2:30][CH2:31]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 912824-Oxo-1-phenylcyclohexanenitrileHCID 27603511-(3-Phenoxypropyl)piperazineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 867482974-(3-Phenoxypropyl]piperazinyl-1-phenylcyclohexanecarbonitrileYield 50%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

5.0 g (0.025 mol) of 4-cyano-4-phenylcyclohexanone and 5.5 g (0.025 mol) of 3-phenoxypropylpiperazine were dissolved with 3.0 g of acetic acid in 70 ml of ethanol and then, while stirring at room temperature, a solution of 1.7 g (0.027 mol) of sodium cyanoborohydride was slowly added dropwise. The mixture was stirred overnight and then diluted with water and extracted with dichloromethane. The organic phase was subsequently washed with dilute acid (pH 4), dilute sodium hydroxide solution and water and finally dried and evaporated. The residue was converted into the hydrochloride with isopropanolic hydrochloric acid, and the product was recrystallized from isopropanol/water. Yield: 50%, C26H33N3O×2 HCl dihydrochloride, melting point >250° C.

Workup

  1. stirringThe mixture was stirred overnight
  2. extractionextracted with dichloromethane
  3. washThe organic phase was subsequently washed
  4. additionwith dilute acid (pH 4), dilute sodium hydroxide solution and water
  5. customfinally dried
  6. customevaporated
  7. customthe product was recrystallized from isopropanol/water

Sources & evidence

ORD record
ord-b5dac46a65ce49dba7ddd599ca0126ae
Source dataset
uspto-grants-1994_12
Patent number
US05371088

Reaction notes

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