Hydrochloric Acid → [3-(Ethylamino)-4-methoxyphenyl]dimethylamine

HRID 475936Notes

Reaction equation

HRID 475936 reaction equation
[CH3:1][N:2]([CH3:15])[C:3]1[CH:4]=[C:5]([NH:11][C:12](=O)[CH3:13])[C:6]([O:9][CH3:10])=[CH:7][CH:8]=1.O.Cl.[OH-].[Na+]>C1COCC1.C(Cl)Cl>[CH2:12]([NH:11][C:5]1[CH:4]=[C:3]([N:2]([CH3:15])[CH3:1])[CH:8]=[CH:7][C:6]=1[O:9][CH3:10])[CH3:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 67430069N-(3-dimethylamino-6-methoxyphenyl)acetamide

Product 1

HCID 59064796[3-(Ethylamino)-4-methoxyphenyl]dimethylamineYield 101.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

N-(3-dimethylamino-6-methoxyphenyl)acetamide 26 (0.10 gm, 0.48 mmoles) was dissolved in 2 ml THF and stirred under argon at room temperature. Borane-methylsulfide complex (0.6 ml, 2.0M, 1.2 mmoles) was added by syringe. After 10 minutes at ambient temperature, the mixture was heated to reflux for 3 hours. After cooling to room temperature, 0.6 ml water was cautiously added with stirring 0.1 ml conc. HCl. After heating for 1 hour, 5 ml DCM and 0.3 ml 2N NaOH were added sequentially with vigorous stirring. The aqueous portion was extracted with three 30 ml portions of DCM which were combined, dried over MgSO4, filtered, and concentrated by rotary evaporation under reduced pressure to give 95 mg of crude [3-(ethylamino)-4-methoxyphenyl]dimethylamine 27.

Workup

  1. additionBorane-methylsulfide complex (0.6 ml, 2.0M, 1.2 mmoles) was added by syringe
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 3 hours
  4. temperatureAfter cooling to room temperature
  5. temperatureAfter heating for 1 hour
  6. extractionThe aqueous portion was extracted with three 30 ml portions of DCM which
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated by rotary evaporation under reduced pressure

Sources & evidence

ORD record
ord-c9ea583917c4471599ae32492fea022c
Source dataset
uspto-grants-2014_01
Patent number
US08637658B2

Reaction notes

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