Potassium Hydroxide → 2-(2-Methoxyphenyl)-N-methylethan-1-amine

HRID 581689Notes

Reaction equation

HRID 581689 reaction equation
C(O[C:6]([NH:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17][CH3:18])=O)(C)(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[K+]>O1CCCC1>[CH3:6][NH:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17][CH3:18]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 14687316HCID 14687316, compoundHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 130925052-(2-Methoxyphenyl)-N-methylethan-1-amineYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To N-(t-Butyloxycarbonyl)-2-(2-methoxyphenyl)-ethylamine (182.7 mmol, 45.9 g) in dry tetrahydrofuran (200 mL) at 0° C. was added, in portions, lithium aluminum hydride (219.2 mmol, 8.3 g) under N2. After stirring at 0° C. for 1 hour, the ice-bath was removed and then the reaction heated to reflux for 24 hours, cooled to room temperature then to 0° C.; the excess lithium aluminum hydride was destroyed very carefully with 20% potassium hydroxide solution (1.3 equivalent). After removing the salt by filtration, the filtrate was dried then evaporated to dryness to give product as a white solid (26.2 g, 87%).

Workup

  1. customthe ice-bath was removed
  2. temperaturethe reaction heated
  3. temperatureto reflux for 24 hours
  4. temperaturecooled to room temperature
  5. customto 0° C.
  6. customAfter removing the salt
  7. filtrationby filtration
  8. customthe filtrate was dried
  9. customthen evaporated to dryness

Sources & evidence

ORD record
ord-7bdd198fd2c54cdbbacc8d539aa6f59a
Source dataset
uspto-grants-1999_07
Patent number
US05922697

Reaction notes

Loading…