Methylhydrazine → HCID 131711075, compound

HRID 2083501Notes

Reaction equation

HRID 2083501 reaction equation
[ClH:1].[CH3:2][N:3]([CH2:5][C:6]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:11][CH2:10][CH2:9][C:8](=[CH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:7]1=O)[CH3:4].[CH3:26][NH:27][NH2:28]>CO>[ClH:1].[CH3:2][N:3]([CH3:4])[CH2:5][C:6]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:7]2[CH:8]([CH:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:27]([CH3:26])[N:28]=2)[CH2:9][CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 131711076HCID 131711076, compound

Product 1

HCID 131711075HCID 131711075, compoundYield 36.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 10.7 g of 2-[(dimethylamino)methyl]-2-phenyl-6-(phenylmethylene)cyclohexanone, monohydrochloride in 70 ml of methanol is treated with 1.5 g of methylhydrazine and the resulting solution is refluxed for 4 hours. The solution is cooled and the solvent is removed on a rotary evaporator to give 13.7 g of a semi-crystalline solid residue, which is crystallized from 30 ml of isopropanol to give 4.2 g of the title compound, melting point 225°-227° C (dec.). An additional 0.77 g of product is recovered from the filtrate giving a total yield of 4.97 g of the title compound, melting point 225°-227° C. Recrystallization of 5.6 g of this material from 100 ml of isopropanol gives 4.8 g of product, melting point 225°-227° C (dec.).

Workup

  1. temperaturethe resulting solution is refluxed for 4 hours
  2. temperatureThe solution is cooled
  3. customthe solvent is removed on a rotary evaporator
  4. customto give 13.7 g of a semi-crystalline solid residue, which
  5. customis crystallized from 30 ml of isopropanol

Sources & evidence

ORD record
ord-007680de0142424fbe847404f16320a9
Source dataset
uspto-grants-1978_04
Patent number
US04085280

Reaction notes

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