Water → 2-((3,4-Dihydro-2,2-dimethyl-4-phenyl-2H-1-benzopyran-7-yl)oxy)-N,N-dimethylethanamine

HRID 614740

Reaction equation

HRID 614740 reaction equation
[CH3:1][C:2]1([CH3:19])[CH2:11][CH:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][C:6]([OH:18])=[CH:7][CH:8]=2)[O:3]1.[H-].[Na+].[CH3:22][N:23]([CH3:27])[CH2:24][CH2:25]Cl.O>C1(C)C=CC=CC=1>[CH3:1][C:2]1([CH3:19])[CH2:11][CH:10]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:9]2[C:4](=[CH:5][C:6]([O:18][CH2:25][CH2:24][N:23]([CH3:27])[CH3:22])=[CH:7][CH:8]=2)[O:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 79012-Chloro-N,N-dimethylethylamineHCID 24758Sodium hydrideHCID 205705312,2-Dimethyl-7-hydroxy-4-phenylchroman

Product 1

HCID 104286962-((3,4-Dihydro-2,2-dimethyl-4-phenyl-2H-1-benzopyran-7-yl)oxy)-N,N-dimethylethanamine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2,2-dimethyl-7-hydroxy-4-phenylchroman (3.72 g), sodium hydride (0.53 g, 60% dispersion in oil) and 2-dimethylaminoethyl chloride (1.58 g) in toluene (59 ml) was stirred and boiled under reflux for 6 hours. Water was added to the cooled mixture and the organic layer was separated and extracted with 5N hydrochloric acid (3 × 30 ml). The combined acid extract was basified, extracted with ether and the ether extract dried (magnesium sulphate). Removal of the solvent gave 2,2-dimethyl-7-dimethylaminoethoxy-4-phenylchroman which was isolated as its hydrochloride salt, m.p. 165°-167° C.

Workup

  1. temperatureunder reflux for 6 hours
  2. customthe organic layer was separated
  3. extractionextracted with 5N hydrochloric acid (3 × 30 ml)
  4. extractionThe combined acid extract
  5. extractionextracted with ether
  6. extractionthe ether extract
  7. dry with materialdried (magnesium sulphate)
  8. customRemoval of the solvent

Sources & evidence

ORD record
ord-7463360d25394477830da7721887bb44
Source dataset
uspto-grants-1979_03
Patent number
US04146539

Linked notes

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