Methylhydrazine → Farnesylamine

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

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.