Acetic Anhydride → HCID 14969550, compound

HRID 266808Notes

Reaction equation

HRID 266808 reaction equation
[C:1](OC(=O)C)(=[O:3])C.[NH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:38]=[CH:37][C:17]([C:18]([N:20]2[CH2:25][CH2:24][CH:23]([N:26]3[C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[CH2:30][CH2:29][C:27]3=[O:28])[CH2:22][CH2:21]2)=[O:19])=[CH:16][CH:15]=1>C(O)=O>[CH:1]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:15]=[CH:16][C:17]([C:18]([N:20]2[CH2:25][CH2:24][CH:23]([N:26]3[C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[CH2:30][CH2:29][C:27]3=[O:28])[CH2:22][CH2:21]2)=[O:19])=[CH:37][CH:38]=1)=[O:3]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 14969545HCID 14969545, compound

Product 1

HCID 14969550HCID 14969550, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A mixture of formic acid (0.19 ml) and acetic anhydride (0.4 ml) is stirred with heating at 50°-60° C. for 1.5 hour. Thereto is added 1-{1-[4-(4-aminobutoxy)benzoyl]-4-piperidinyl}-3,4-dihydrocarbostyril (0.6 g) at room temperature and the mixture is stirred at room temperature for 13 hours. The reaction mixture is poured into ice-water and extracted with ethyl acetate. The extract is washed with aqueous sodium hydrogen carbonate, water and saline solution and dried with sodium sulfate. The solvent is distilled off and the resulting residue is purified by silica gel column chromatography (solvent: dichloromethane:methanol=50:1→25:1) to give 1-{1-[4-(4-formylaminobutoxy)benzoyl]-4-piperidinyl}-3,4-dihydrocarbostyril (0.49 g).

Workup

  1. temperaturewith heating at 50°-60° C. for 1.5 hour
  2. stirringthe mixture is stirred at room temperature for 13 hours
  3. extractionextracted with ethyl acetate
  4. washThe extract is washed with aqueous sodium hydrogen carbonate, water and saline solution
  5. dry with materialdried with sodium sulfate
  6. distillationThe solvent is distilled off
  7. customthe resulting residue is purified by silica gel column chromatography (solvent: dichloromethane:methanol=50:1→25:1)

Sources & evidence

ORD record
ord-5351803b9ae54d7db7b5c0e5bbb47871
Source dataset
uspto-grants-1997_07
Patent number
US05652247

Reaction notes

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