Diethylamine → 1-(2,2-Diethoxyethyl)cyclohexane-1-carbonitrile

HRID 1682163Notes

Reaction equation

HRID 1682163 reaction equation
C(NCC)C.C([Li])CCC.[CH:11]1([C:17]#[N:18])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.[CH2:19]([O:21][CH:22]([O:25][CH2:26][CH3:27])[CH2:23]Br)[CH3:20]>CCCCCC>[CH2:19]([O:21][CH:22]([O:25][CH2:26][CH3:27])[CH2:23][C:11]1([C:17]#[N:18])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)[CH3:20]

Participants

6

Reactant 4

HCID 8021DiethylamineHCID 69834CyanocyclohexaneHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 178418339Butyllithium

Product 1

HCID 132173501-(2,2-Diethoxyethyl)cyclohexane-1-carbonitrile

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
-70 °C

Procedure

51.7 ml (0.5 mol) of anhydrous diethylamine are added dropwise, under protective gas at -10° C., to 312.5 ml (0.5 mol) of a 15% strength solution of n-butyllithium in hexane. The mixture is stirred for 20 minutes and then cooled to -70° C. 54.6 g of cyclohexanecarbonitrile are added dropwise over the course of 30 minutes and, after a further 30 minutes, 98.5 g of bromoacetaldehyde diethyl acetal are added within 1 hour and the mixture is left at low temperature for 24 hours. It is then warmed to room temperature, 100 g of ice are added, and the mixture is extracted twice with 500 ml of ethyl acetate, and the organic phase is dried over sodium sulfate, evaporated in vacuo and the residue is subjected to vacuum distillation.

Workup

  1. waitthe mixture is left at low temperature for 24 hours
  2. temperatureIt is then warmed to room temperature
  3. extractionthe mixture is extracted twice with 500 ml of ethyl acetate
  4. dry with materialthe organic phase is dried over sodium sulfate
  5. customevaporated in vacuo
  6. distillationthe residue is subjected to vacuum distillation

Sources & evidence

ORD record
ord-7b802bb3bfd4452cac497edaa52dc315
Source dataset
uspto-grants-1992_12
Patent number
US05175306

Reaction notes

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