2-Chloro-N,N-dimethylethylamine → 2,2-Dimethyl-7-(2-dimethylaminoethoxy)-4-(1-naphthyl)chroman

HRID 26281

Reaction equation

HRID 26281 reaction equation
[CH3:1][C:2]1([CH3:23])[CH2:11][CH:10]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][C:6]([OH:22])=[CH:7][CH:8]=2)[O:3]1.[H-].[Na+].[CH3:26][N:27]([CH3:31])[CH2:28][CH2:29]Cl>C1(C)C=CC=CC=1.O>[CH3:1][C:2]1([CH3:23])[CH2:11][CH:10]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][C:6]([O:22][CH2:29][CH2:28][N:27]([CH3:31])[CH3:26])=[CH:7][CH:8]=2)[O:3]1

Participants

6

Reactant 3

HCID 79012-Chloro-N,N-dimethylethylamineHCID 24758Sodium hydrideHCID 205705012,2-Dimethyl-4-(1-naphthyl)-7-chromanol

Product 1

HCID 205705522,2-Dimethyl-7-(2-dimethylaminoethoxy)-4-(1-naphthyl)chromanYield 67.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

To a stirred solution of 2,2-dimethyl-4-(1-naphthyl)-7-chromanol (7.48 g) in dry toluene (50 ml) was added sodium hydride (1.5 g, ~1.5 eq., 60% dispersion in oil) and the mixture was brought to reflux. To the resulting solution was added dropwise over 10 minutes a solution of 2-dimethylaminoethyl chloride (2.70 g, ~1.1 eq.) in dry toluene (10 ml) and the mixture was stirred under reflux for 2 hours, cooled, diluted with water and left to stand overnight. Next day the toluene layer was separated and evaporated in vacuo. The aqueous layer was extracted with ether and the extract used to dissolve the residue from the toluene evaporation. The organic layer was extracted with 5 N hydrochloric acid (45, 35 and 20 ml respectively), the combined acid extract was basified and extracted into ether. After being dried the ether was removed in vacuo to give a yellow oil (6.2 g) which was chromatographed on alumina in 8% ether--92 % petroleum ether (b.p. 60-80) to give the title compound (4.71 g, 51%) as a colourless oil. The hydrochloric salt had m.p. 178.5°-181.5° C.

Workup

  1. temperatureto reflux
  2. temperatureunder reflux for 2 hours
  3. temperaturecooled
  4. waitleft
  5. customNext day the toluene layer was separated
  6. customevaporated in vacuo
  7. extractionThe aqueous layer was extracted with ether
  8. dissolutionto dissolve the residue
  9. customfrom the toluene evaporation
  10. extractionThe organic layer was extracted with 5 N hydrochloric acid (45, 35 and 20 ml respectively), the combined acid
  11. extractionextract
  12. extractionextracted into ether
  13. dry with materialAfter being dried the ether
  14. customwas removed in vacuo

Sources & evidence

ORD record
ord-f7c28d4637364a36915b735482d1d856
Source dataset
uspto-grants-1979_04
Patent number
US04148909

Linked notes

Loading…