Dimethylamine → 1-(4-benzylthiophenyl)-2-[2-(N,N-dimethylamino)ethoxy]ethanol hydrochloride

HRID 976519Notes

Reaction equation

HRID 976519 reaction equation
[CH2:1]([S:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([OH:21])[CH2:16][O:17][CH2:18][CH2:19][Cl:20])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:22][NH:23][CH3:24].[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>O.C(OCC)(=O)C.C(O)C>[ClH:20].[CH2:1]([S:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([OH:21])[CH2:16][O:17][CH2:18][CH2:19][N:23]([CH3:24])[CH3:22])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 674Dimethylamine2×HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 537562141-(4-Benzylthiophenyl)-2-(2-chloroethoxy)ethanol

Product 1

HCID 216432711-(4-benzylthiophenyl)-2-[2-(N,N-dimethylamino)ethoxy]ethanol hydrochloride

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 600 mg of 1-(4-benzylthiophenyl)-2-(2-chloroethoxy)ethanol, 4ml of a 50% aqueous dimethylamine solution, 310 mg of potassium iodide and 5 ml of ethanol was refluxed for 4 hours. To the reaction mixture was further added 4 ml of a 50% aqueous dimethylamine solution. The reaction mixture was cooled to room temperature. The solvent was removed by distillation under reduced pressure. To the residue thus obtained were added 30 ml of ethyl acetate and 30 ml of water. The resulting 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. The residue was dissolved in 15 ml of acetone. To the solution was added 0.4 ml of a 5N dry hydrogen chloride-ethanol solution. The resulting crystals were collected by filtration to obtain 590 mg of 1-(4-benzylthiophenyl)-2-[2-(N,N-dimethylamino)ethoxy]ethanol hydrochloride (compound No. 222).

Workup

  1. temperaturewas refluxed for 4 hours
  2. customThe solvent was removed by distillation under reduced pressure
  3. customTo the residue thus obtained
  4. customThe organic layer was separated
  5. washwashed with water
  6. dry with materiala saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate
  7. customThe solvent was removed by distillation under reduced pressure
  8. dissolutionThe residue was dissolved in 15 ml of acetone
  9. additionTo the solution was added 0.4 ml of a 5N dry hydrogen chloride-ethanol solution
  10. filtrationThe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-dc156f2172aa471a8fea92a9847108f0
Source dataset
uspto-grants-1997_03
Patent number
US05612381

Reaction notes

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