Water → HCID 19928725, compound

HRID 1708956Notes

Reaction equation

[CH3:1][NH:2][CH:3]([C:6]([CH3:19])([OH:18])[CH2:7][CH2:8][CH2:9][CH:10]([CH3:17])[CH2:11][CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[CH2:4][OH:5].N1C=CC=CC=1.Cl.[C:27](Cl)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[N:30][CH:29]=1.O>ClC(Cl)C>[CH3:1][N:2]([CH:3]([C:6]([OH:18])([CH3:19])[CH2:7][CH2:8][CH2:9][CH:10]([CH3:17])[CH2:11][CH2:12][CH2:13][CH:14]([CH3:15])[CH3:16])[CH2:4][OH:5])[C:27](=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[N:30][CH:29]=1

Participants

Conditions

Temperature: -30 °C

Procedure

In 100 ml of dichloroethane were dissolved 10 g of 2-(methylamino)-3,7,11-trimethyl-1,3-dodecanediol and 8.7 g of pyridine and the solution was cooled to -30° C. To this solution was added 7.2 g of nicotinoyl chloride hydrochloride gradually and the mixture was stirred at room temperature for 3 hours. After the reaction was completed, the reaction mixture was poured into water and extracted with dichloroethane. The organic layer was washed with aqueous sodium hydrogen carbonate and after drying over anhydrous magnesium sulfate, the solvent was distilled off. Finally, the residue was subjected to silica gel column chromatography (elution with ethanol) to give 12.0 g of N-methyl-N-(1,3-dihydroxy3,7,11-trimethyldodecan-2-yl)nicotinamide [Compound (66)]. Yield 93%.

Workup

extractionextracted with dichloroethane
washThe organic layer was washed with aqueous sodium hydrogen carbonate
dry with materialafter drying over anhydrous magnesium sulfate
distillationthe solvent was distilled off
washFinally, the residue was subjected to silica gel column chromatography (elution with ethanol)

Sources & evidence

ORD record: ord-f75c27e803b64466891dc00d889c520f
Source dataset: uspto-grants-1990_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04946857

Reaction notes

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