Sodium Hydroxide → alpha,alpha-Dimethyl-2-naphthaleneethanamine

HRID 895876Notes

Reaction equation

HRID 895876 reaction equation
[CH3:1][C:2]([NH:15]C(OCC1C=CC=CC=1)=O)([CH3:14])[CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=1.[OH-].[Na+]>CO.O.[OH-].[OH-].[Pd+2]>[CH3:14][C:2]([NH2:15])([CH3:1])[CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 9923712n-[2-Methyl-1-(naphthalen-2-yl)propan-2-yl]-benzyloxycarboxamide

Product 1

HCID 15369616alpha,alpha-Dimethyl-2-naphthaleneethanamineYield 97.2%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

Palladium hydroxide on carbon (19.7 g) was suspended in methanol (500 ml), to the suspension was added a solution of N-[2-methyl-1-(naphthalen-2-yl)propan-2-yl]-benzyloxycarboxamide (237.6 g) obtained in Step 11 in methanol (2 L), and a hydrogenation reaction was performed at room temperature overnight. After filtration of the reaction mixture, the filtrate was concentrated under reduced pressure. To the obtained residue was added ethyl acetate, and to the solution was added conc. hydrochloric acid (70 ml) to give crystals. The obtained crystals were suspended in water, and after an addition of 4N aqueous sodium hydroxide solution (350 ml), the mixture was extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give crystals of the title compound (138 g).

Workup

  1. customa hydrogenation reaction
  2. filtrationAfter filtration of the reaction mixture
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionTo the obtained residue was added ethyl acetate
  5. additionto the solution was added conc. hydrochloric acid (70 ml)
  6. customto give crystals
  7. extractionthe mixture was extracted with ethyl acetate
  8. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0856403203a44a96911111b04ce39c7f
Source dataset
uspto-grants-2005_07
Patent number
US06916956B2

Reaction notes

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