Dimethylamine → 1-(6-benzyloxy-2-naphthyl)-2-[2-(N,N-dimethylamino)ethoxy]ethanol

HRID 862528Notes

Reaction equation

HRID 862528 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([CH:19]([OH:25])[CH2:20][O:21][CH2:22][CH2:23]Cl)[CH:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I-].[K+].[CH3:28][NH:29][CH3:30].C(O)C>C(OCC)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([CH:19]([OH:25])[CH2:20][O:21][CH2:22][CH2:23][N:29]([CH3:30])[CH3:28])[CH:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 674Dimethylamine2×HCID 702EthanolHCID 4875Potassium IodideHCID 54204419HCID 54204419, compound

Product 1

HCID 544081981-(6-benzyloxy-2-naphthyl)-2-[2-(N,N-dimethylamino)ethoxy]ethanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 4.5 g of 1-(6-benzyloxy-2-naphthyl)-2-(2-chloroethoxy)ethanol, 1 g of potassium iodide, 10 ml of a 50% aqueous dimethylamine solution and 20 ml of ethanol was refluxed for 3 hours. To the reaction mixture was added 10 ml of a 50% aqueous dimethylamine solution. The resulting mixture was further refluxed for 6 hours. The reaction mixture was cooled and concentrated to about a half volume under reduced pressure. To the concentrate were added 100 ml of ethyl acetate and 100 ml of water. The mixture was adjusted to pH 10.5 with potassium carbonate. The organic layer was separated, 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. To the residue thus obtained was added 30 ml of diethyl ether. The resulting crystals were collected by filtration and dried to obtain 3.9 g of 1-(6-benzyloxy-2-naphthyl)-2-[2-(N,N-dimethylamino)ethoxy]-ethanol (compound No. 284).

Workup

  1. temperaturewas refluxed for 3 hours
  2. temperatureThe resulting mixture was further refluxed for 6 hours
  3. temperatureThe reaction mixture was cooled
  4. concentrationconcentrated to about a half volume under reduced pressure
  5. additionTo the concentrate were added 100 ml of ethyl acetate and 100 ml of water
  6. customThe organic layer was separated
  7. washwashed with water
  8. dry with materiala saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate
  9. customThe solvent was removed by distillation under reduced pressure
  10. customTo the residue thus obtained
  11. filtrationThe resulting crystals were collected by filtration
  12. customdried

Sources & evidence

ORD record
ord-be13a7701e43490a88e94b1a66af9359
Source dataset
uspto-grants-1998_02
Patent number
US05719150

Reaction notes

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