Hydrochloric Acid → Ethyl N-[2-(4-hydroxyphenyl)ethyl]carbamate

HRID 601572Notes

Reaction equation

HRID 601572 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[NH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1.[OH-].[Na+].Cl>O1CCCC1.O>[CH2:5]([O:4][C:2](=[O:3])[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)[CH3:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5610TyramineHCID 10928Ethyl chloroformateHCID 14798Sodium Hydroxide

Product 1

HCID 2762412Ethyl N-[2-(4-hydroxyphenyl)ethyl]carbamateYield 84.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Add dropwise via an addition funnel a solution of ethyl chloroformate (0.74 mL, 7.7 mmol) in tetrahydrofuran (7 mL) to a stirred solution of tyramine (1.0 g, 7.3 mmol), sodium hydroxide (0.7 g, 17.1 mmol), and water (7 mL). Stir at room temperature for 18 hours then pour the reaction into 1N aqueous hydrochloric acid so the pH=1-2. Extract with ethyl acetate (3×25 mL). Dry the combined ethyl acetate extracts over sodium chloride/magnesium sulfate, filter, and concentrate on a rotary evaporator to yield 1.3 g, 6.2 mmol of [2-(4-hydroxy-phenyl)-ethyl]-carbamic acid ethyl ester: 1H NMR (CDCl3, 300.00 MHz): 7.01 (d, 2H); 6.78 (d, 2H); 6.26 (s, 1H); 4.78 (s, 1H); 4.14-4.09 (m, 2H); 3.40-3.38 (m, 2H); 2.74-2.69 (m, 2H); 1.24-1.19 (m, 3H).

Workup

  1. additionthen pour
  2. extractionExtract with ethyl acetate (3×25 mL)
  3. dry with materialDry the combined ethyl acetate
  4. filtrationfilter
  5. concentrationconcentrate on a rotary evaporator

Sources & evidence

ORD record
ord-2a8a5e853188419d9ddba97f6734b95f
Source dataset
uspto-grants-2011_03
Patent number
US07902372B2

Reaction notes

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