Water → O-(2-methoxybenzyl)-6-dimethylaminohexanol

HRID 272796

Reaktionsgleichung

Reaktionsgleichung von HRID 272796
[CH3:1][N:2]([CH3:10])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9].[H-].[Na+].O.[CH3:14][O:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH2:18]Cl>O1CCCC1>[CH3:14][O:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH2:18][O:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][N:2]([CH3:10])[CH3:1]

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 746236-Dimethylaminohexan-1-olHCID 814952-(Chloromethyl)anisole

Produkt 1

HCID 23436782O-(2-methoxybenzyl)-6-dimethylaminohexanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

6-(Dimethylamino)hexanol (8.80 g, 60.6 mmol) was dissolved in an anhydrous 2:1 mixture of tetrahydrofuran and dimethylfornamide (150 mL) and the solution was cooled in an ice bath. Sodium hydride (60% in oil, 3.23 g, 80.8 mmol) was added in portions and after 5 min. the water bath was removed. After 45 min., 2-methoxybenzyl chloride (6.28 g, 40.4 mmol) was added. After 4 h, the reaction mixture was quenched with 1 M sodium thiosulfate and tetrahydrofuran was removed in vacuo. The reaction mixture was washed with ethyl acetate and the aqueous phase was basified with 3 M sodium hydroxide, followed by extraction with ether. The ether layer was dried over potassium carbonate, filtered and acidified with 4 M hydrochloric acid in dioxane. The reaction mixture was concentrated in vacuo and the residue was crystallized form ethanol/ether to give O-(2-methoxybenzyl)-6-dimethylaminohexanol as the hydrochloride salt (10.4 g, 85%). MS (M-Cl)+266.3.

Aufarbeitung

  1. temperaturethe solution was cooled in an ice bath
  2. customwas removed
  3. waitAfter 4 h
  4. customthe reaction mixture was quenched with 1 M sodium thiosulfate and tetrahydrofuran
  5. customwas removed in vacuo
  6. washThe reaction mixture was washed with ethyl acetate
  7. extractionfollowed by extraction with ether
  8. dry with materialThe ether layer was dried over potassium carbonate
  9. filtrationfiltered
  10. concentrationThe reaction mixture was concentrated in vacuo
  11. customthe residue was crystallized form ethanol/ether

Quellen und Nachweise

ORD-Eintrag
ord-6aff08e24c004d02b3a693f66a0b9f8b
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07456203B2

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