HCID 20572046, compound → HCID 20572047, compound

HRID 1577290Notes

Reaction equation

HRID 1577290 reaction equation
Br[CH2:2][C:3]([CH3:11])([CH3:10])[CH2:4][C:5]([CH3:9])([CH3:8])[C:6]#[N:7].[CH3:12][Li]>CCOCC>[CH3:12][C:6]1[C:5]([CH3:9])([CH3:8])[CH2:4][C:3]([CH3:11])([CH3:10])[CH2:2][N:7]=1

Participants

4

Reactant 2

HCID 20572046HCID 20572046, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 20572047HCID 20572047, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To 22 g of 5-bromo-2,2,4,4-tetramethyl pentane nitrile in 60 ml of anhydrous ether, 0.1 mol of methyl lithium in solution in 200 ml of anhydrous ether is added drop by drop in an inert atmosphere. The reaction medium is maintained between 0° and 5° C. during the addition and then for an additional 30 minutes and then kept at room temperature for 4 hours. After hydrolysis, the aqueous phase is extracted with ether. The 2,3,3,5,5-pentamethyl-3,4,5,6-tetrahydropyridine is then isolated by distillation. There is obtained a colorless liquid of B.P.10 -2 =43° C. in a yield of 70% of Δ1-piperideine.

Workup

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

Sources & evidence

ORD record
ord-3ed63d412143430db7c376866d94fae1
Source dataset
uspto-grants-1981_09
Patent number
US04287337

Reaction notes

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