Acrylonitrile → 3-(4,4-Diphenylpiperidin-1-yl)propionitrile

HRID 396604Notes

Reaction equation

HRID 396604 reaction equation
Cl.[C:2]1([C:8]2([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(CC)CC.[C:27](#[N:30])[CH:28]=[CH2:29]>CCO>[C:2]1([C:8]2([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:9][CH2:10][N:11]([CH2:29][CH2:28][C:27]#[N:30])[CH2:12][CH2:13]2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7855AcrylonitrileHCID 8471TriethylamineHCID 30475044,4-Diphenylpiperidine hydrochloride

Product 1

HCID 155128643-(4,4-Diphenylpiperidin-1-yl)propionitrileYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 4,4-diphenylpiperidine hydrochloride (195 mg, 0.712 mmol, 1.0 equiv) in EtOH (1.5 mL) was added Et3N (0.25 mL, 1.8 mmol, 2.6 equiv) followed by acrylonitrile (0.13 mL, 2.01 mmol, 2.8 equiv). The resulting solution was stirred at room temperature under argon for 15 minutes and then concentrated. Water was added, and the mixture was extracted three times with EtOAc. The combined organic extracts were dried over MgSO4 and concentrated to give 170 mg (87%) of tan solid, which was characterized spectroscopically and used for the next reaction without purification.

Workup

  1. concentrationconcentrated
  2. additionWater was added
  3. extractionthe mixture was extracted three times with EtOAc
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4f4dbe5cf560473baab6c6b701c8d57b
Source dataset
uspto-grants-2003_08
Patent number
US06608086B2

Reaction notes

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