Hydrochloric Acid → 3,4-di-O-nicotinoyl-N-carbobenzoxydopamine

HRID 5906

Reaction equation

HRID 5906 reaction equation
[C:1]([NH:11][CH2:12][CH2:13][C:14]1[CH:21]=[CH:20][C:18]([OH:19])=[C:16]([OH:17])[CH:15]=1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].Cl.[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[N:26][CH:25]=1>N1C=CC=CC=1>[C:23]([O:17][C:16]1[CH:15]=[C:14]([CH:21]=[CH:20][C:18]=1[O:19][C:23](=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[N:26][CH:25]=1)[CH2:13][CH2:12][NH:11][C:1]([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2])(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[N:26][CH:25]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 82604Nicotinoyl chlorideHCID 11108946Benzyl N-[2-(3,4-dihydroxyphenyl)ethyl]carbamate

Product 1

HCID 1317181713,4-di-O-nicotinoyl-N-carbobenzoxydopamineYield 71.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

19.0 g (66 mmol) of N-carbobenzoxydopamine obtained in Synthetic Example 1-(1) and 37.2 g (209 mmol) of hydrochloride of nicotinoyl chloride were added to 200 ml of pyridine. After stirring at room temperature for 12 hours, the mixture was allowed to react at 35°-40° C. for 2 hours. Then, the reaction mixture was poured into ice and a sodium carbonate solution followed by extraction with chloroform. The resulting extract was dried over anhydrous magnesium sulfate and the solvent was distilled off to obtain crude crystals. The thus-obtained crystals were recrystallized from ethyl acetate/diethyl ether (1:5 by volume) to obtain 23.5 g (yield: 71.6%) of the desired compound in the form of white crystals (m.p. 77°-78° C.).

Workup

  1. customto react at 35°-40° C. for 2 hours
  2. additionThen, the reaction mixture was poured into ice
  3. extractiona sodium carbonate solution followed by extraction with chloroform
  4. extractionThe resulting extract
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off
  7. customto obtain crude crystals
  8. customThe thus-obtained crystals were recrystallized from ethyl acetate/diethyl ether (1:5 by volume)

Sources & evidence

ORD record
ord-904e0eff30db466b8a5980cfec8f75e8
Source dataset
uspto-grants-1993_09
Patent number
US05246949

Linked notes

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