5-chloro-2,2-dimethylpentanenitrile → 3,4,5,6-Tetrahydro-2,3,3-trimethylpyridine

HRID 1577291Notes

Reaction equation

HRID 1577291 reaction equation
[CH3:1][Li].Cl[CH2:4][CH2:5][CH2:6][C:7]([CH3:11])([CH3:10])[C:8]#[N:9]>CCOCC>[CH3:1][C:8]1[C:7]([CH3:11])([CH3:10])[CH2:6][CH2:5][CH2:4][N:9]=1

Participants

4

Reactant 2

HCID 2642175-chloro-2,2-dimethylpentanenitrileHCID 178418348HCID 178418348, compound

Product 1

HCID 131577763,4,5,6-Tetrahydro-2,3,3-trimethylpyridine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

0.1 mol of methyl lithium dissolved in 200 ml of ether anhydride is added drop by drop in an inert atmosphere (argon or nitrogen) to 15 g of 5-chloro-2,2-dimethyl pentane nitrile diluted in 60 ml of anhydrous ether. The reaction mixture is maintained between 0° and 5° C. during the addition and then for a further 30 minutes and then kept at room temperature for 4 hours. After hydrolysis it is extracted with ether. The 2,3,3-trimethyl-3,4,5,6-tetrahydropyridine is then isolated by distillation. A colorless liquid of B.P.14 =60° C. is obtained in a yield of 76% of 1-piperideine.

Workup

  1. temperatureThe reaction mixture is maintained between 0° and 5° C. during the addition
  2. waitkept at room temperature for 4 hours
  3. customAfter hydrolysis it
  4. extractionis extracted with ether

Sources & evidence

ORD record
ord-5cf60033b1114b4991f12c32ea544805
Source dataset
uspto-grants-1981_09
Patent number
US04287337

Reaction notes

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