Hydrochloric Acid → Benzyl N-[2-(3,4-dihydroxyphenyl)ethyl]carbamate

HRID 5903

Reaction equation

HRID 5903 reaction equation
B([O-])([O-])[O-].[Na+].[Na+].[Na+].Cl.[NH2:9][CH2:10][CH2:11][C:12]1[CH:19]=[CH:18][C:16]([OH:17])=[C:14]([OH:15])[CH:13]=1.[OH-].[Na+].[CH2:22]([O:29][C:30](Cl)=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.Cl>O>[C:30]([NH:9][CH2:10][CH2:11][C:12]1[CH:19]=[CH:18][C:16]([OH:17])=[C:14]([OH:15])[CH:13]=1)([O:29][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:31]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide2×HCID 65340Dopamine HydrochlorideHCID 159383boric acid, sodium salt

Product 1

HCID 11108946Benzyl N-[2-(3,4-dihydroxyphenyl)ethyl]carbamateYield 96.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
15 °C

Procedure

38.2 g (100 mmol) of sodium borate and 18.9 g (100 mmol) of dopamine hydrochloride were dissolved in 250 ml of water. To the solution thus obtained, was added a 2 N sodium hydroxide solution under a nitrogen gas stream to adjust the pH value to 9. Then 17.1 g (100 mmol) of benzyloxycarbonyl chloride was added dropwise thereto while stirring at 15° C. for 4 hours. Simultaneously, a 2 N sodium hydroxide solution was added to maintain the pH value of the reaction mixture to 9. After continuing the stirring for 2 hours, the mixture was adjusted to pH 1 to 2 with hydrochloric acid and then extracted with diethyl ether. Next, it was dried over anhydrous magnesium sulfate and the solvent was distilled off. After washing the residue with petroleum ether, the crude crystals thus obtained were recrystallized from ethanol/n-hexane (1 : 1 by volume). Thus 27.6 g (yield: 96.5% of the desired compound (m.p.: 134°- 135 ° C.) was obtained in the form of white crystals.

Workup

  1. customTo the solution thus obtained
  2. temperatureto maintain the pH value of the reaction mixture to 9
  3. customstirring for 2 hours
  4. extractionextracted with diethyl ether
  5. dry with materialNext, it was dried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off
  7. washAfter washing the residue with petroleum ether
  8. customthe crude crystals thus obtained
  9. customwere recrystallized from ethanol/n-hexane (1 : 1 by volume)

Sources & evidence

ORD record
ord-bd3436a3a9104be29be12b6fb5ed6ff9
Source dataset
uspto-grants-1993_09
Patent number
US05246949

Linked notes

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