Diisopropylethylamine → HCID 67450427, compound

HRID 2368084Notes

Reaction equation

HRID 2368084 reaction equation
Cl.[CH3:2][CH:3]([NH:12][C:13](=[O:15])[CH3:14])[CH2:4][CH2:5][CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1.Cl[C:17]1[O:18][C:19]2[CH:25]=[C:24]([OH:26])[CH:23]=[CH:22][C:20]=2[N:21]=1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[OH:26][C:24]1[CH:23]=[CH:22][C:20]2[N:21]=[C:17]([N:9]3[CH2:8][CH2:7][CH:6]([CH2:5][CH2:4][CH:3]([NH:12][C:13](=[O:15])[CH3:14])[CH3:2])[CH2:11][CH2:10]3)[O:18][C:19]=2[CH:25]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 234412462-Chloro-1,3-benzoxazol-6-OLHCID 67449164HCID 67449164, compound

Product 1

HCID 67450427HCID 67450427, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-[1-methyl-3-(piperidin-4-yl)propyl]acetamide hydrochloride (500 mg), 2-chloro-1,3-benzoxazol-6-ol (361 mg) and N,N-diisopropylethylamine (826 mg) in DMF (15 mL) was stirred at 100° C. for 10 hr. The reaction mixture was allowed to cool, and the solvent was evaporated under reduced pressure. The residue was diluted with ethyl acetate/THF mixed solvent (10/1), and the solution was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (543 mg).

Workup

  1. temperatureto cool
  2. customthe solvent was evaporated under reduced pressure
  3. additionThe residue was diluted with ethyl acetate/THF mixed solvent (10/1)
  4. washthe solution was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-4e66ce45b31b4c8cbaa8a3c91d15f9ec
Source dataset
uspto-grants-2014_04
Patent number
US08703758B2

Reaction notes

Loading…