Sodium hydride → HCID 54182312, compound

HRID 2083009Notes

Reaction equation

HRID 2083009 reaction equation
[CH:1](=[C:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C:9]1=[N:14][OH:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:19][CH:20]([CH3:23])[CH2:21]Cl.[CH3:24][N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1>C1(C)C=CC=CC=1>[CH:1](=[C:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C:9]1=[N:14][O:15][CH2:19][CH:20]([CH3:23])[CH2:21][N:28]1[CH2:29][CH2:30][N:25]([CH3:24])[CH2:26][CH2:27]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 531671-MethylpiperazineHCID 955661-Bromo-3-chloro-2-methylpropaneHCID 189199HCID 189199, compound

Product 1

HCID 54182312HCID 54182312, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Conditions

Temperature
80 °C

Procedure

The solution of 20.1 g (0.1 moles) of 2-benzalcyclohexanone oxime in 200 ml of anhydrous toluene is dropwise added at 85° C, under continuous stirring, to the suspension of 2.4 g (0.1 moles) of sodium hydride in 50 ml of anhydrous toluene. After boiling the reaction mixture for 2 hours, 18.86 g (0.11 moles) of 1-bromo-3-chloro-2-methylpropane are added, and the reaction mixture is boiled for a few hours. After cooling the mixture to 80° C, a solution of 11 g (0.11 moles) of N-methylpiperazine in 20 ml of anhydrous toluene is dropwise added and the reaction mixture is kept for further 6 hours at this temperature. After cooling and washing with water, a solution of 22 g of fumaric acid in 220 ml of anhydrous ethanol is poured to the toluene solution, the mixture is cooled, and the precipitated crystals are filtered off. Yield in difumarate: 48 g (81.7%); m.p. 190°-191° C. The produce is identical with that described in Example 11.

Workup

  1. customfor 2 hours
  2. waitthe reaction mixture is boiled for a few hours
  3. temperatureAfter cooling
  4. washwashing with water
  5. additiona solution of 22 g of fumaric acid in 220 ml of anhydrous ethanol is poured to the toluene solution
  6. temperaturethe mixture is cooled
  7. filtrationthe precipitated crystals are filtered off
  8. customYield in difumarate

Sources & evidence

ORD record
ord-4c1d867b5b4e4b93b6d0d0860211a37e
Source dataset
uspto-grants-1978_04
Patent number
US04083978

Reaction notes

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