Tyramine → Benzyl [2-(4-hydroxyphenyl)ethyl]carbamate

HRID 2258020Notes

Reaction equation

HRID 2258020 reaction equation
C(=O)(O)[O-].[Na+].[NH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1.Cl[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18]>O>[C:17]([NH:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18]

Participants

5

Reactant 3

HCID 5610Tyramine2×HCID 10387Benzyl chloroformateHCID 516892Sodium Bicarbonate

Product 1

HCID 14103856Benzyl [2-(4-hydroxyphenyl)ethyl]carbamate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium bicarbonate (12.6 g) was dissolved in distilled water (250 ml) and tyramine (20.6 g) added. The resulting suspension was heated to boiling to dissolve the tyramine, then cooled to room temperature. Benzyl chloroformate (25.6 g) was added while stirring and with occasional vigorous shaking. After stirring and shaking for an additional 1.5 hours, the precipitate was filtered off and washed with distilled water. The solid was dissolved in ether (250 ml) and washed with distilled water. The organic layer was dried over MgSO4 and evaporated in vacuo to give a residue which solidified upon cooling. Recrystallization from ether/hexane gave the desired product as colourless crystals, m.p. 96°-98° C.

Workup

  1. temperatureThe resulting suspension was heated
  2. stirringAfter stirring
  3. stirringshaking for an additional 1.5 hours
  4. filtrationthe precipitate was filtered off
  5. washwashed with distilled water
  6. dissolutionThe solid was dissolved in ether (250 ml)
  7. washwashed with distilled water
  8. dry with materialThe organic layer was dried over MgSO4
  9. customevaporated in vacuo
  10. customto give a residue which
  11. temperatureupon cooling
  12. customRecrystallization from ether/hexane

Sources & evidence

ORD record
ord-3afe07b95ec34f1e873de09e09ef3be5
Source dataset
uspto-grants-1997_08
Patent number
US05658944

Reaction notes

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