1,1-Dimethylhydrazine → HCID 69788121, compound

HRID 488732Notes

Reaction equation

HRID 488732 reaction equation
[CH3:1][N:2]([CH3:4])[NH2:3].[Br:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][C:14]2=O)=[CH:8][CH:7]=1>CCO>[CH3:1][N:2]([CH3:4])[N:3]=[C:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH:13]1[CH2:12][C:9]1[CH:8]=[CH:7][C:6]([Br:5])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 59761,1-DimethylhydrazineHCID 22268065HCID 22268065, compound

Product 1

HCID 69788121HCID 69788121, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Anhydrous N,N-dimethylhydrazine (17 ml) (3,7 eq.) was quickly poured in a solution of 2-[(4-bromophenyl)methyl]-cyclohexanone (16 g) (0.06 mol) in EtOH (200 ml). The reaction mixture was refluxed for 10 h, then concentrated to dryness. The residue was partitioned between tBuOMe and water, the organic phase washed twice with water, dried over magnesium sulfate and concentrated to yield 2-[(4-bromophenyl)methyl]-cyclohexanone dimethylhydrazone (16 g) as a yellow oil. 1H NMR (CDCl3): 7.35 (2H, d), 7.05 (2H, d), 3.05 (1H, dd), 2.4 (6H,s), 2.7-2.2 (4H, m), 1.8-1.3 (6H, m).

Workup

  1. temperatureThe reaction mixture was refluxed for 10 h
  2. concentrationconcentrated to dryness
  3. customThe residue was partitioned between tBuOMe and water
  4. washthe organic phase washed twice with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5cdf70d7eb5742ab97e05d6a0d647549
Source dataset
uspto-grants-2005_12
Patent number
US06974815B2

Reaction notes

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