1-Naphthaleneacetonitrile → 8-Piperidino-2-(1-naphthyl)-octanenitrile

HRID 620185

Reaction equation

HRID 620185 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][CH2:24][CH2:25][CH2:26][CH2:27]Cl)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>CCOCC>[N:16]1([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH:13]([C:3]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH:6]=[CH:5][CH:4]=2)[C:14]#[N:15])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 85961-NaphthaleneacetonitrileHCID 24533Sodium amideHCID 138060031-(6-Chlorohexyl)piperidine

Product 1

HCID 212458678-Piperidino-2-(1-naphthyl)-octanenitrile

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

3.9 g of sodium amide are added in small quantities to 16.7 g of 1-naphthyl-acetonitrile in solution in 200 ml of anhydrous ether. After 2 hours of heating to reflux, 20.5 g of 6-piperidino-1-chloro-hexane are added and heating is continued to reflux for another 5 hours. Then, using the conventional methods, 30 g of product are isolated.

Workup

  1. temperatureAfter 2 hours of heating
  2. temperatureto reflux
  3. temperatureheating
  4. temperatureto reflux for another 5 hours
  5. customare isolated

Sources & evidence

ORD record
ord-d01eca2758cf4f3cb0af6e293f6d41bb
Source dataset
uspto-grants-1989_04
Patent number
US04820717

Linked notes

Loading…