Ethanolamine → HCID 59341474, compound

HRID 15245

Reaction equation

HRID 15245 reaction equation
[CH2:1]([C:8]([N:20]([CH3:22])[CH3:21])([CH2:18][CH3:19])[C:9]([C:11]1[CH:16]=[CH:15][C:14](F)=[CH:13][CH:12]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:23]([CH2:25][NH2:26])[OH:24].C(=O)([O-])[O-].[K+].[K+]>CC(N(C)C)=O.O>[CH2:1]([C:8]([N:20]([CH3:22])[CH3:21])([CH2:18][CH3:19])[C:9]([C:11]1[CH:16]=[CH:15][C:14]([NH:26][CH2:25][CH2:23][OH:24])=[CH:13][CH:12]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 700EthanolamineHCID 11430Potassium CarbonateHCID 193605992-Benzyl-2-(dimethylamino)-1-(4-fluorophenyl)butan-1-one

Product 1

HCID 59341474HCID 59341474, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
140 °C

Procedure

44.9 g (0.15 mol) 2-Benzyl-1-(4-fluorophenyl)-2-dimethylamino-1-butanone and 61.08 g (1.05 mol) ethanolamine are dissolved in 400 ml dimethylacetamide. 41.5 (0.3 mol) Potassium carbonate are added and the suspension is heated to 140° C. while stirring. The reaction mixture is kept at this temperature during 16 hours, cooled to room temperature and diluted with water. The aqueous phase is several times extracted with ethyl acetate, the combined organic extracts washed with water and dried over magnesium sulfate. Evaporation of the solvent gives the crude product as a yellowish-brown oil. The product is purified by chromatography on silica gel (eluent: petroleum ether/ethyl acetate 2:1→1:1). The fractions containing the product are collected to give a slightly yellowish solid product. Recrystallisation from ethyl acetate/hexane gave 2-benzyl-1-[4-(2-hydroxyethylamino)phenyl]-2-dimethylamino-1-butanone as slightly yellowish crystals melting at 109-111° C. Yield: 34.7 g (68%). 1H-NMR data are in agreement with the proposed structure.

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washthe combined organic extracts washed with water
  4. dry with materialdried over magnesium sulfate
  5. customEvaporation of the solvent
  6. customgives the crude product as a yellowish-brown oil
  7. customThe product is purified by chromatography on silica gel (eluent: petroleum ether/ethyl acetate 2:1→1:1)
  8. additionThe fractions containing the product
  9. customare collected
  10. customto give a slightly yellowish solid product
  11. customRecrystallisation from ethyl acetate/hexane

Sources & evidence

ORD record
ord-3d5c76a6ecfa4060aa28c6ae79dff7db
Source dataset
uspto-grants-2010_06
Patent number
US07732504B2

Linked notes

Loading…