Sodium Hydroxide → 3-Amino-2-(7-methoxy-1-naphthyl)-1-propanol hydrochloride

HRID 2374726Notes

Reaction equation

HRID 2374726 reaction equation
[Cl-:1].[Al+3].[Cl-].[Cl-].[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:11]([CH:13]([C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[C:25]([O:28][CH3:29])[CH:26]=2)[CH:21]=[CH:20][CH:19]=1)[C:14](OC)=[O:15])#[N:12].[OH-].[Na+]>CCOCC>[ClH:1].[NH2:12][CH2:11][CH:13]([C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[C:25]([O:28][CH3:29])[CH:26]=2)[CH:21]=[CH:20][CH:19]=1)[CH2:14][OH:15]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 15149128Methyl cyano(7-methoxy-1-naphthyl)acetateHCID 21226445Aluminium lithium hydride

Product 1

HCID 685970113-Amino-2-(7-methoxy-1-naphthyl)-1-propanol hydrochloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

Aluminium chloride (80 mmol), dissolved in 200 ml of anhydrous ether, is added to a suspension of lithium aluminium hydride at 0° C. in 300 ml of anhydrous ether. After stirring for 10 minutes, the compound obtained in Step A (20 mmol), dissolved in 200 ml of anhydrous ether, is added. After 30 minutes, the mixture is hydrolyzed, with caution and in the cold state, using sodium hydroxide solution (10 g; 40 ml). The precipitate formed is then filtered off and washed with copious amounts of ether. The residue obtained after evaporation is taken up in water and the aqueous phase is extracted with dichloromethane. The organic phase is then washed with water, dried and decolored, and is then treated with gaseous hydrogen chloride and evaporated. The oil obtained is precipitated from ethyl acetate, and the precipitate formed is filtered off under suction and then recrystallized to yield the title product in the form of a white solid.

Workup

  1. additionis added
  2. waitAfter 30 minutes
  3. customThe precipitate formed
  4. filtrationis then filtered off
  5. washwashed with copious amounts of ether
  6. customThe residue obtained
  7. customafter evaporation
  8. extractionthe aqueous phase is extracted with dichloromethane
  9. washThe organic phase is then washed with water
  10. customdried
  11. additionis then treated with gaseous hydrogen chloride
  12. customevaporated
  13. customThe oil obtained
  14. customis precipitated from ethyl acetate
  15. customthe precipitate formed
  16. filtrationis filtered off under suction
  17. customrecrystallized

Sources & evidence

ORD record
ord-d246222b33794adb91c8d61dc924061a
Source dataset
uspto-grants-2008_12
Patent number
US07462741B2

Reaction notes

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