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

HRID 1275223Notes

Reaction equation

HRID 1275223 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 (0.195 g, 0.712 mmol) in EtOH (1.5 mL) was added Et3N (0.25 mL, 1.8 mmol, 2.6 eq) followed by acrylonitrile (0.13 mL, 2.01 mmol, 2.8 eq). The resulting solution was stirred at room temperature under argon for 15 min and then concentrated. Water was added, and the mixture was extracted with EtOAc (3×10 mL). The combined organic extracts were dried (MgSO4) and concentrated to give 170 mg (87%) of a tan solid, which was characterized spectroscopically and used in the next reaction without purification.

Workup

  1. concentrationconcentrated
  2. additionWater was added
  3. extractionthe mixture was extracted with EtOAc (3×10 mL)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-493ca0477c754938b8bd348e9bce9d4d
Source dataset
uspto-grants-2000_12
Patent number
US06159990

Reaction notes

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