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

HRID 2121008Notes

Reaction equation

HRID 2121008 reaction equation
[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.CN(C)C=O>[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

6-(Dimethylamino)hexanol (8.80 g, 60.6 mmol) was dissolved in an anhydrous 2:1 mixture of tetrahydrofuran and dimethylformamide (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.

Workup

  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

Sources & evidence

ORD record
ord-b9022976d72b400dab7976857e94bbc2
Source dataset
uspto-grants-2004_02
Patent number
US06693202B1

Reaction notes

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