1-Naphthaleneacetonitrile → 2-(Naphthalen-1-yl)-4-(piperidin-1-yl)butanenitrile

HRID 620186Notes

Reaction equation

HRID 620186 reaction equation
[NH2-].[Na+].[C:3]1([CH2:13][C:14]#[N:15])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.[N:16]1([CH2:22][CH2:23]Cl)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>CCOCC.O>[C:3]1([CH:13]([CH2:23][CH2:22][N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[C:14]#[N:15])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 85961-NaphthaleneacetonitrileHCID 24533Sodium amideHCID 748271-(2-Chloroethyl)piperidine

Product 1

HCID 141712-(Naphthalen-1-yl)-4-(piperidin-1-yl)butanenitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

8.2 g of sodium amide are added in small quantities on a solution of 33.4 g of 1-naphthyl acetonitrile in 450 ml of anhydrous ether. The mixture is heated for 2 hours to reflux, then 29.5 g of 2-piperidino-1-chloroethane are added, a heating to reflux is repeated for 5 hours. The mixture is then cooled, poured in water, and the organic phase is extracted 3 times with 600 ml of hydrochloric acid at 10%. The aqueous phase is washed with ether and neutralized with soda at 30%. The decanting oil is extracted, washed with sodium chloride-saturated water and dried over magnesium sulphate. After evaporation of the solvent, the resulting oil is distilled under reduced pressure (vane pump).

Workup

  1. temperatureThe mixture is heated for 2 hours
  2. temperatureto reflux
  3. temperaturea heating to reflux
  4. temperatureThe mixture is then cooled
  5. extractionthe organic phase is extracted 3 times with 600 ml of hydrochloric acid at 10%
  6. washThe aqueous phase is washed with ether and neutralized with soda at 30%
  7. extractionThe decanting oil is extracted
  8. washwashed with sodium chloride-saturated water
  9. dry with materialdried over magnesium sulphate
  10. customAfter evaporation of the solvent
  11. distillationthe resulting oil is distilled under reduced pressure (vane pump)

Sources & evidence

ORD record
ord-362806f4ff914b018c2cef575c633584
Source dataset
uspto-grants-1989_04
Patent number
US04820717

Reaction notes

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