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

HRID 1198242Notes

Reaction equation

HRID 1198242 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, 4 ml 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 resulting mixture was refluxed for 4 hours. 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. temperaturewas refluxed for 4 hours
  3. customwas removed by distillation under reduced pressure
  4. customTo the residue thus obtained
  5. customThe organic layer was separated
  6. washwashed with water
  7. dry with materiala saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate
  8. customThe solvent was removed by distillation under reduced pressure
  9. dissolutionThe residue was dissolved in 15 ml of acetone
  10. additionTo the solution was added 0.4 ml of a 5N dry hydrogen chloride-ethanol solution
  11. filtrationThe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-c4fb1963767549488ccb7454be6c3aca
Source dataset
uspto-grants-1994_01
Patent number
US05280032

Reaction notes

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