Ethanolamine → HCID 44464684, compound

HRID 453272Notes

Reaction equation

HRID 453272 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:9]=[C:8]([CH3:10])[N:7]([C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([O:21][CH3:22])[CH:17]=3)[CH:12]=2)[N:6]=1.[CH2:23]([CH2:25][NH2:26])[OH:24].[Na+].[I-].O>CN1CCCC1=O.C(OCC)(=O)C>[CH3:22][O:21][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[CH:12]=[C:11]([N:7]1[C:8]([CH3:10])=[CH:9][C:5]([O:4][CH2:3][CH2:2][NH:26][CH2:25][CH2:23][OH:24])=[N:6]1)[CH:20]=[CH:19]2

Participants

7

Reactant 4

HCID 700EthanolamineHCID 962WaterHCID 5238Sodium IodideHCID 46221334HCID 46221334, compound

Product 1

HCID 44464684HCID 44464684, compoundYield 41.1%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 3-(2-chloroethoxy)-5-methyl-1-(6-methoxynaphthalen-2-yl)-1H-pyrazol (0.15 g, 0.47 mmol), ethanolamine (0.115 g, 1.89 mmol) and catalytic amount of NaI in N-methylpyrrolidone (NMP) (30 ml) was heated to 110° C., in a nitrogen atmosphere, during 20 hrs. Next, it was cooled, and water and ethyl acetate was added to the residue. The organic phase was washed with water several times, dried over Na2SO4, filtered and evaporated, thereby leaving a residue of 66 mg of 2-(2-(1-(6-Methoxynaphthalen-2-yl)-5-methyl-1H-pyrazol-3-yloxy)ethylamino)etanol. The aqueous phase was extracted with dichloromethane, dried over Na2SO4, filtered and evaporated leaving a crude residue, which was purified by a silica gel column chromatography (eluent: ethyl acetate/methanol, from 8/2 until 0/10) thereby obtaining additional 40 mg of desired compound. A total weight of 104 mg (yield: 65%) of 2-(2-(1-(6-methoxynaphthalen-2-yl)-5-methyl-1H-pyrazol-3-yloxy)ethylamino)etanol in the form of a colourless oil was obtained.

Workup

  1. temperatureNext, it was cooled
  2. washThe organic phase was washed with water several times
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-7786ba96ed854236b92a67d8ccd13536
Source dataset
uspto-grants-2013_07
Patent number
US08492425B2

Reaction notes

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