Methylhydrazine → Farnesylamine

HRID 249125Notes

Reaction equation

HRID 249125 reaction equation
[CH3:1][C:2]([CH2:16][CH2:17][CH:18]=[C:19]([CH3:26])[CH2:20][CH2:21][CH:22]=[C:23]([CH3:25])[CH3:24])=[CH:3][CH2:4][N:5]1C(=O)C2C(=CC=CC=2)C1=O.CNN.[OH-].[Na+]>C(O)C>[CH2:4]([NH2:5])[CH:3]=[C:2]([CH2:16][CH2:17][CH:18]=[C:19]([CH2:20][CH2:21][CH:22]=[C:23]([CH3:25])[CH3:24])[CH3:26])[CH3:1]

Participants

5

Reactant 3

HCID 6061MethylhydrazineHCID 14798Sodium HydroxideHCID 542051882-(3,7,11-Trimethyl-2,6,10-dodecatrienyl)-1H-isoindole-1,3(2H)-dione

Product 1

HCID 3080630FarnesylamineYield 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution 2.50 g (7.1 mmol) of Part (1) compound in 15 ml of absolute ethanol at room temperature under argon was treated with 1.9 ml (35.57 mmol, 5.0 eq.) of methyl hydrazine and stirred for 2 hours at room temperature and 4 hours at reflux. After cooling and the addition of 7.1 ml (7.1 mmol, 1.0 eq.) of 1M NaOH, the ethanol was removed under reduced pressure. The residue was extracted with 350 ml of ethyl ether and the ether layer washed with 100 ml of lM NaOH, 50 ml of H2O and 50 ml of brine, dried (MgSO4) and evaporated to obtain 1.45 g of crude product. Purification by bulb-to-bulb distillation at 120° C./0.005 mm provided 1.405 g (89%) of title compound as a colorless oil.

Workup

  1. temperatureat reflux
  2. temperatureAfter cooling
  3. customthe ethanol was removed under reduced pressure
  4. extractionThe residue was extracted with 350 ml of ethyl ether
  5. washthe ether layer washed with 100 ml of lM NaOH, 50 ml of H2O and 50 ml of brine
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customto obtain 1.45 g of crude product
  9. customPurification
  10. distillationby bulb-to-bulb distillation at 120° C./0.005 mm

Sources & evidence

ORD record
ord-74dae765f8204675be713a5ad2f4aedb
Source dataset
uspto-grants-1993_05
Patent number
US05212164

Reaction notes

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