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Water → HCID 19928725, compound

HRID 1885211
Notes
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Reaction equation

HRID 1885211 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 199287142-(N-Methylamino)-3,7,11-trimethyl-1,3-dodecanediol

Product 1

HCID 19928725HCID 19928725, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6365
1,1-Dichloroethane
Solvent

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-dihydroxy-3,7,11-trimethyldodecan-2-yl)nicotinamide [Compound (66)]. Yield 93%.

Workup

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

Sources & evidence

ORD record
ord-476268ff3e9f45abacfff9fc6722308b
Source dataset
uspto-grants-1992_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05143921

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes