Ammonia → HCID 131718020, compound

HRID 266816Notes

Reaction equation

HRID 266816 reaction equation
C(OC(C1C=CC(C([N:12]2[CH2:17][CH2:16][CH:15]([N:18]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH2:22][CH2:21][C:19]3=[O:20])[CH2:14][CH2:13]2)=O)=CC=1)=N)C.[NH3:31].[CH3:32][OH:33]>>[C:32]([C:15]1([N:18]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH2:22][CH2:21][C:19]2=[O:20])[CH2:16][CH2:17][NH:12][CH2:13][CH2:14]1)(=[O:33])[NH2:31]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 19030802HCID 19030802, compound

Product 1

HCID 131718020HCID 131718020, compound

Procedure

1-{1-[4-(1-Ethoxy-1-iminomethyl)benzoyl]-4-piperidinyl}-3,4-dihydrocarbostyril (1 g) is dissolved in methanol (10 ml) and thereto is added aqueous ammonia (10 ml) and the mixture is stirred at room temperature overnight. The solvent is concentrated and water is added to the residue. The mixture is extracted with chloroform, dried with sodium carbonate, concentrated and then purified by silica gel column chromatography (solvent: chloroform:methanol=10:1) and recrystallized from ethanol/n-hexane to give 1-[1-(4-carbamoyl-4-piperidinyl]-3,4-dihydrocarbostyril (0.2 g) as white powder, m.p.: 101°-104° C.

Workup

  1. concentrationThe solvent is concentrated
  2. additionwater is added to the residue
  3. extractionThe mixture is extracted with chloroform
  4. dry with materialdried with sodium carbonate
  5. concentrationconcentrated
  6. custompurified by silica gel column chromatography (solvent: chloroform:methanol=10:1)
  7. customrecrystallized from ethanol/n-hexane

Sources & evidence

ORD record
ord-d00f4054f6ec4a188a07d999e4a83b03
Source dataset
uspto-grants-1997_07
Patent number
US05652247

Reaction notes

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