HCID 19031237, compound → HCID 19031173, compound

HRID 1648556Notes

Reaction equation

HRID 1648556 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH:14]1[CH2:19][CH2:18][N:17]([C:20](=[O:31])[C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:22]=3[O:29][CH3:30])[CH2:16][CH2:15]1)[C:9](=[O:32])[CH2:8][CH2:7]2)([O-])=O>[C].[Pd].C(O)(=O)C>[NH2:1][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH:14]1[CH2:15][CH2:16][N:17]([C:20](=[O:31])[C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:22]=3[O:29][CH3:30])[CH2:18][CH2:19]1)[C:9](=[O:32])[CH2:8][CH2:7]2

Participants

4

Reactant 1

HCID 19031237HCID 19031237, compound

Product 1

HCID 19031173HCID 19031173, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 10 % palladium-carbon (0.4 g) and acetic acid (50 ml) is added to 6-nitro-1-[1-(2,4-dimethoxybenzoyl)-4-piperidinyl]-3,4-dihydrocarbostyril (4.0 g) and the mixture is subjected to catalytic reduction at 70° C. for 1 hour. The catalyst is filtered off and the filtrate is concentrated. The resulting residue is basified with 10 % aqueous sodium hydroxide solution and extracted with dichloromethane. The solvent is concentrated and the resulting residue is purified by silica gel column chromatography (solvent; dichloromethane:methanol=20:1) to give 6-amino-1-[1-(2,4-dimethoxybenzoyl)-4-piperidinyl]-3,4-dihydrocarbostyril (1.9 g).

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe filtrate is concentrated
  3. extractionextracted with dichloromethane
  4. concentrationThe solvent is concentrated
  5. customthe resulting residue is purified by silica gel column chromatography (solvent; dichloromethane:methanol=20:1)

Sources & evidence

ORD record
ord-10618cb57b064c26ac36cfa53ff2d3f2
Source dataset
uspto-grants-1995_07
Patent number
US05436254

Reaction notes

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