L-Tartaric acid → HCID 86743296, compound

HRID 1722738Notes

Reaction equation

HRID 1722738 reaction equation
[CH3:1][N:2]([CH3:13])[C:3]([C:8]1[S:9][CH:10]=[CH:11][CH:12]=1)([CH2:6][CH3:7])[CH2:4][OH:5].[C:14]([OH:23])(=[O:22])[C@@H:15]([C@H:17]([C:19]([OH:21])=[O:20])[OH:18])[OH:16]>CO>[CH3:13][N:2]([CH3:1])[C:3]([C:8]1[S:9][CH:10]=[CH:11][CH:12]=1)([CH2:6][CH3:7])[CH2:4][OH:5].[C:14]([O-:23])(=[O:22])[C@@H:15]([C@H:17]([C:19]([O-:21])=[O:20])[OH:18])[OH:16]

Participants

4

Reactant 2

HCID 444305L-Tartaric acidHCID 10512214HCID 10512214, compound

Product 1

HCID 86743296HCID 86743296, compoundYield 66.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Dimethylamino-2-(2-thienyl)-1-butanol (11.2 g) and L-(+)-tartaric acid (4.2 g) are dissolved in methanol with heating and the solution is concentrated to remove solvent. Ethanol is added to the residue and the mixture is allowed to stand overnight. The precipitates are collected by filtration and recrystallized from ethanol, whereby (+)-2- dimethylamino-2-(2-thienyl)-1-butanol·L-(+)-tartarate (6.5 g) is obtained. An aqueous potassium carbonate solution is added to the salt and the mixture is extracted with chloroform. The extract is dried and concentrated to remove solvent. The residue is crystallized with n-hexane, whereby (+)-2-dimethylamino-2-(2-thienyl)-1-butanol (2.7 g) is obtained.

Workup

  1. temperaturewith heating
  2. concentrationthe solution is concentrated
  3. customto remove solvent
  4. additionEthanol is added to the residue
  5. filtrationThe precipitates are collected by filtration
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-47e82338ceee4bcfaabe1466ca3f7683
Source dataset
uspto-grants-1989_08
Patent number
US04857543

Reaction notes

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