Water → N-ethyl-N-(4-hydroxybutyl)-6-methoxy-1,2,3,4-tetrahydro-2-naphthylamine

HRID 1732990Notes

Reaction equation

HRID 1732990 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:9]([CH:18]1[CH2:27][CH2:26][C:25]2[C:20](=[CH:21][CH:22]=[C:23]([O:28][CH3:29])[CH:24]=2)[CH2:19]1)[C:10](=O)[CH2:11][CH2:12][C:13](OC)=[O:14])[CH3:8].O.[OH-].[Na+]>O1CCCC1>[CH2:7]([N:9]([CH:18]1[CH2:27][CH2:26][C:25]2[C:20](=[CH:21][CH:22]=[C:23]([O:28][CH3:29])[CH:24]=2)[CH2:19]1)[CH2:10][CH2:11][CH2:12][CH2:13][OH:14])[CH3:8]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 12843097N-ethyl-N-[3-(methoxycarbonyl)propionyl]-6-methoxy-1,2,3,4-tetrahydro-2-naphthylamineHCID 21226445Aluminium lithium hydride

Product 1

HCID 12843106N-ethyl-N-(4-hydroxybutyl)-6-methoxy-1,2,3,4-tetrahydro-2-naphthylamineYield 85.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of 8.3 g of lithium aluminum hydride and 200 ml of anhydrous tetrahydrofuran, a solution of 14.5 g of N-ethyl-N-[3-(methoxycarbonyl)propionyl]-6-methoxy-1,2,3,4-tetrahydro-2-naphthylamine in 100 ml of anhydrous tetrahydrofuran was added dropwise. After heating the resulting solution for 4.5 hours at reflux, a mixed solution of 8.3 ml of water and 50 ml of tetrahydrofuran as added dropwise to the solution under cooling with ice. Then, 8.3 ml of a 15% sodium hydroxide aqueous solution was added dropwise to the resulting solution and lastly 25 ml of water was added dropwise thereto to precipitate insoluble materials. After removing the insoluble materials by filtration, the filtrate was concentrated under reduced pressure to obtain a residue. After the residue was extracted with benzene, the benzene layer was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 10.8 g of N-ethyl-N-(4-hydroxybutyl)-6-methoxy-1,2,3,4-tetrahydro-2-naphthylamine as a colorless oily product. This product was treated with an ethanolic solution of hydrogen chloride having a concentration of about 18% to obtain N-ethyl-N-(4-hydroxybutyl)-6-methoxy-1,2,3,4-tetrahydro-2-naphthylamine hydrochloride as colorless crystals having a melting point of 124°-126° C.

Workup

  1. temperatureAfter heating the resulting solution for 4.5 hours
  2. temperatureat reflux
  3. temperatureunder cooling with ice
  4. additionwas added dropwise
  5. customto precipitate insoluble materials
  6. customAfter removing the insoluble materials
  7. filtrationby filtration
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customto obtain a residue
  10. extractionAfter the residue was extracted with benzene
  11. washthe benzene layer was washed with water
  12. dry with materialdried over anhydrous sodium sulfate
  13. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7e4521f62e13498e894096b1726d6b49
Source dataset
uspto-grants-1980_12
Patent number
US04239903

Reaction notes

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