Hydrochloric Acid → 2-[2-(N,N-dimethylamino)ethoxy]-1-(1-naphthyl)ethanol hydrochloride

HRID 362963Notes

Reaction equation

HRID 362963 reaction equation
CC(C)([O-])C.[K+].[CH3:7][N:8]([CH2:10][CH2:11][OH:12])[CH3:9].[C:13]1([CH:23]2[CH2:25][O:24]2)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1.[ClH:26]>CC(C)=O.C(OCC)(=O)C>[ClH:26].[CH3:7][N:8]([CH2:10][CH2:11][O:12][CH2:25][CH:23]([C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1)[OH:24])[CH3:9]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 79022-(Dimethylamino)ethanolHCID 64543662-(Naphthalen-1-yl)oxiraneHCID 23665647Potassium tert-butoxide

Product 1

HCID 675980182-[2-(N,N-dimethylamino)ethoxy]-1-(1-naphthyl)ethanol hydrochloride

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 13.2 g of potassium tert-butoxide and 47.2 ml of 2-(N,N-dimethylamino)ethanol was heated to 80° C. Thereto was dropwise added 40.0 g of 2-(1-naphthyl)oxirane in 3.5 hours. The resulting mixture was stirred for 1.5 hours at 80°-85° C. The reaction mixture was cooled and added to a mixture of 100 ml of ethyl acetate and 100 ml of ice water. The resulting mixture was adjusted to pH 11.5 with 6N hydrochloric acid. The organic layer was separated. The aqueous layer was extracted with 50 ml of ethyl acetate. The extract was combined with the previously separated organic layer. The combined organic layer was washed with water and a saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue thus obtained was subjected to distillation to obtain a fraction having a boiling point of 152°-163° C./0.6-0.8 mmHg. The oily product obtained was dissolved in 200 ml of acetone. Into the solution was blown hydrogen chloride gas with ice cooling. The resulting crystals were collected by filtration, washed with acetone, and dried to obtain 22.7 g of 2-[2-(N,N-dimethylamino)ethoxy]-1-(1-naphthyl)ethanol hydrochloride (compound No. 228).

Workup

  1. customin 3.5 hours
  2. temperatureThe reaction mixture was cooled
  3. customThe organic layer was separated
  4. extractionThe aqueous layer was extracted with 50 ml of ethyl acetate
  5. washThe combined organic layer was washed with water
  6. dry with materiala saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate
  7. customThe solvent was removed by distillation under reduced pressure
  8. customThe residue thus obtained
  9. distillationwas subjected to distillation
  10. customto obtain a fraction
  11. customThe oily product obtained
  12. filtrationThe resulting crystals were collected by filtration
  13. washwashed with acetone
  14. customdried

Sources & evidence

ORD record
ord-cf47f3711f724ff0be3069a04a02027d
Source dataset
uspto-grants-1999_02
Patent number
US05872117

Reaction notes

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