Acetic Acid → HCID 19030851, compound

HRID 1648561Notes

Reaction equation

HRID 1648561 reaction equation
Br.C(O)(=O)C.C(O[C:11]([N:13]([C:15]1[CH:39]=[CH:38][C:18]([C:19]([N:21]2[CH2:26][CH2:25][CH:24]([N:27]3[C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[CH2:31][CH2:30][C:28]3=[O:29])[CH2:23][CH2:22]2)=[O:20])=[CH:17][CH:16]=1)C)=O)(C)(C)C.C(=O)([O-])[O-].[K+].[K+]>O>[CH3:11][NH:13][C:15]1[CH:16]=[CH:17][C:18]([C:19]([N:21]2[CH2:22][CH2:23][CH:24]([N:27]3[C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[CH2:31][CH2:30][C:28]3=[O:29])[CH2:25][CH2:26]2)=[O:20])=[CH:38][CH:39]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 11430Potassium CarbonateHCID 18960741HCID 18960741, compound

Product 1

HCID 19030851HCID 19030851, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture (5 ml) of hydrobromic acid and acetic acid (35 % solution) is added to 1-{1-[4-(N-t-butoxycarbonyl-N-methylamino)benzoyl]-4-piperidinyl}-3,4-dihyrocarbostyril (1.8 g) and the mixture is stirred at room temperature overnight. The reaction mixture is poured into water and the pH value thereof is adjusted to pH 12-14 by adding potassium carbonate. The mixture is extracted with chloroform, dried with sodium carbonate and then purified by silica gel column chromatography (solvent; n-hexane:ethyl acetate=1:1). The resultant is recrystallized from n-hexane/ethanol to give 1-{1-[4-(N-methylamino)benzoyl]-4-piperidinyl}-3,4-dihydrocarbostyril (1.2 g), as white powder, m.p. 184°-186° C.

Workup

  1. extractionThe mixture is extracted with chloroform
  2. dry with materialdried with sodium carbonate
  3. custompurified by silica gel column chromatography (solvent; n-hexane:ethyl acetate=1:1)
  4. customThe resultant is recrystallized from n-hexane/ethanol

Sources & evidence

ORD record
ord-3335bc8c187e439797f88b04ea94ffbc
Source dataset
uspto-grants-1995_07
Patent number
US05436254

Reaction notes

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