Methyl [2-(4-hydroxyphenyl)ethyl]carbamate → N-Methyltyramine

HRID 130907Notes

Reaction equation

HRID 130907 reaction equation
CO[C:3](=O)[NH:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:3][NH:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 20596424Methyl [2-(4-hydroxyphenyl)ethyl]carbamateHCID 21226445Aluminium lithium hydride

Product 1

HCID 9727N-MethyltyramineYield 70.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

Add dropwise via an addition funnel a solution of [2-(4-Hydroxy-phenyl)-ethyl]-carbamic acid methyl ester (13.0 g, 62.2 mmol) in tetrahydrofuran (100 mL) to a stirred solution at 0° C. of 1.0M lithium aluminum hydride in tetrahydrofuran (156 mL) and tetrahydrofuran (250 mL). Reflux for 18 hours, cool to 0° C., quench with saturated aqueous ammonium chloride then stir at room temperature for 3 hours. Filter off the aluminum salts, concentrate on a rotary evaporator, and dry under vacuum to yield 6.6 g of 4-(2-methylamino-ethyl)-phenol: 1H NMR (DMSO-d6, 300.00 MHz): 6.97 (d, 2H); 6.65 (d, 2H); 2.65-2.55 (m, 4H); 2.28 (s, 3H).

Workup

  1. temperatureReflux for 18 hours
  2. customquench with saturated aqueous ammonium chloride
  3. filtrationFilter off the aluminum salts
  4. concentrationconcentrate on a rotary evaporator
  5. customdry under vacuum

Sources & evidence

ORD record
ord-4a2b357b0b5c4add830278e10821ab33
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Reaction notes

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