2-(Benzylmethylamino)-3,7,11-trimethyl-3,7-dodecanediol → 2-(Methylamino)-3,7,11-trimethyl-3,7-dodecanediol

HRID 1708958Notes

Reaction equation

HRID 1708958 reaction equation
C([CH2:8][NH:9][CH:10]([C:12]([CH3:26])([OH:25])[CH2:13][CH2:14][CH2:15][C:16]([CH3:24])([OH:23])[CH2:17][CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21])[CH3:11])C1C=CC=CC=1>[Pd].C(O)C>[CH3:8][NH:9][CH:10]([C:12]([CH3:26])([OH:25])[CH2:13][CH2:14][CH2:15][C:16]([CH3:24])([OH:23])[CH2:17][CH2:18][CH2:19][CH:20]([CH3:21])[CH3:22])[CH3:11]

Participants

4

Reactant 1

HCID 199287442-(Benzylmethylamino)-3,7,11-trimethyl-3,7-dodecanediol

Product 1

HCID 199287162-(Methylamino)-3,7,11-trimethyl-3,7-dodecanediolYield 65%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

An autoclave was charged with 7.5 g of 2-(benzylmethylamino)-3,7,11-trimethyl-3,7-dodecanediol, 0.75 g of palladium-on-carbon and 30 ml of ethanol, and the reaction was conducted at 40° C. under hydrogen pressure (10 atm). After completion of the reaction, the ethanol was distilled off and the residue was subjected to silica gel column chromatography (elution with 95% ethanol-5% triethylamine) to give 3.6 g of 2-(methylamino)-3,7,11-trimethyl-3,7-dodecanediol [Compound (70)]. Yield 65%.

Workup

  1. customwas conducted at 40° C. under hydrogen
  2. customAfter completion of the reaction
  3. distillationthe ethanol was distilled off
  4. washthe residue was subjected to silica gel column chromatography (elution with 95% ethanol-5% triethylamine)

Sources & evidence

ORD record
ord-9eb4fb669f5346e584de986b7c1906e9
Source dataset
uspto-grants-1990_08
Patent number
US04946857

Reaction notes

Loading…