Propionic Acid → N-[2-(1,2,3,7,8,9-hexahydro-2-oxoindeno[5,4-b][1,4]oxazin-9-yl)ethyl]propionamide

HRID 324649Notes

Reaction equation

HRID 324649 reaction equation
Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.[C:24]([OH:28])(=O)[CH2:25][CH3:26].[NH2:29][CH2:30][CH2:31][CH:32]1[C:44]2[C:43]3[NH:42][C:41](=[O:45])[CH2:40][O:39][C:38]=3[CH:37]=[CH:36][C:35]=2[CH2:34][CH2:33]1>CN(C)C=O.O>[O:45]=[C:41]1[CH2:40][O:39][C:38]2[CH:37]=[CH:36][C:35]3[CH2:34][CH2:33][CH:32]([CH2:31][CH2:30][NH:29][C:24](=[O:28])[CH2:25][CH3:26])[C:44]=3[C:43]=2[NH:42]1

Participants

7

Reactant 4

HCID 1032Propionic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 111281719-(2-aminoethyl)-1,7,8,9-tetrahydro-indeno[5,4-b][1,4]oxazin-2(3H)-one

Product 1

HCID 11011664N-[2-(1,2,3,7,8,9-hexahydro-2-oxoindeno[5,4-b][1,4]oxazin-9-yl)ethyl]propionamideYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (372.0 mg, 1.9 mmol.) and 1-hydroxybenzotriazole monohydrate (257 mg, 1.9 mmol.) were suspended in N,N-dimethylformamide (2.5 mL). To the suspension was added, under ice-cooling, propionic acid (0.11 mL, 1.4 mmol.). This reaction mixture was stirred for one hour at room temperature, and, then, cooled again with ice, to which was added dropwise a solution of 9-(2-aminoethyl)-1,7,8,9-tetrahydroindeno[5,4-b][1,4] oxazin-2(3H)-one (300 mg, 1.3 mmol.) in N,N-dimethylformamide (1.5 mL). The mixture was stirred for one hour under ice-cooling. The reaction mixture was poured into water, and the organic matter was extracted with ethyl acetate. The extract solution was dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by means of silica gel column chromatography (chloroform:methanol=10:1) to afford the title compound (yield 253.0 mg, 88%).

Workup

  1. additionTo the suspension was added, under ice-
  2. temperaturecooling
  3. temperaturecooled again with ice, to which
  4. stirringThe mixture was stirred for one hour under ice-
  5. temperaturecooling
  6. extractionthe organic matter was extracted with ethyl acetate
  7. dry with materialThe extract solution was dried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off
  9. customthe residue was purified by means of silica gel column chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-73b11f5f5c74482e8a7744f2f747ea85
Source dataset
uspto-grants-2001_04
Patent number
US06218429B1

Reaction notes

Loading…