Water → HCID 58904646, compound

HRID 1292842Notes

Reaction equation

HRID 1292842 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][O:16][C:17](=[O:28])[NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[O:25][CH2:26][CH3:27])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[C:29](Cl)(=[O:31])[CH3:30].O>C1COCC1>[C:29]([NH:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][O:16][C:17](=[O:28])[NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[O:25][CH2:26][CH3:27])[CH2:12][CH2:13]2)[CH:5]=[CH:6][CH:7]=1)(=[O:31])[CH3:30]

Participants

5

Reactant 3

HCID 962WaterHCID 6367Acetyl chlorideHCID 58904652HCID 58904652, compound

Product 1

HCID 58904646HCID 58904646, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 77 mg (0.2 mmol) of 2-[4-(3-aminophenyl)piperazino]ethyl-N-(2-ethoxyphenyl)carbamate derivative and 44.6 μl (0.32 mmol, 1.6 eq) of TEA in 5 ml of THF, 71 μl (0.3 mmol, 1.5 eq) of acetyl chloride is added. Shaking is carried out at room temperature for about 20 hours. Then H2O is added and the aqueous phase is extracted with CH2Cl2. After drying on Na2SO4 and concentration under vacuum, a white solid is obtained which is purified by column chromatography (eluent CH2Cl2/iPrOH 9:1) to produce 36 mg of the expected product as a brown oil (yield: 43%).

Workup

  1. additionis added
  2. extractionthe aqueous phase is extracted with CH2Cl2
  3. customAfter drying on Na2SO4 and concentration under vacuum
  4. customa white solid is obtained which
  5. customis purified by column chromatography (eluent CH2Cl2/iPrOH 9:1)

Sources & evidence

ORD record
ord-0b8f7ccbf6174a19a94e0e413224d49e
Source dataset
uspto-grants-2007_07
Patent number
US07238693B2

Reaction notes

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