Sulfuric Acid → HCID 19030761, compound

HRID 1708311Notes

Reaction equation

HRID 1708311 reaction equation
[O:1]1C[CH:2]1[CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:33]=[CH:32][C:12]([C:13]([N:15]2[CH2:20][CH2:19][CH:18]([N:21]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH2:25][CH2:24][C:22]3=[O:23])[CH2:17][CH2:16]2)=[O:14])=[CH:11][CH:10]=1.S(=O)(=O)(O)O.[C:39](=[O:42])([O-])O.[Na+]>O1CCOCC1.O>[OH:1][CH:2]([CH2:39][OH:42])[CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]([N:15]2[CH2:16][CH2:17][CH:18]([N:21]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH2:25][CH2:24][C:22]3=[O:23])[CH2:19][CH2:20]2)=[O:14])=[CH:32][CH:33]=1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 19030869HCID 19030869, compound

Product 1

HCID 19030761HCID 19030761, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

1-{1-[4-(4-Oxiranylbutoxy)benzoyl]-4-piperidinyl}-3,4-dihydrocarbostyril (1.6 g) is dissolved in a mixture of dioxane (30 ml) and water (10 ml). Thereto is added conc. sulfuric acid (0.1 ml) and the mixture is stirred at room temperature overnight. The mixture is neutralized with sodium hydrogen carbonate and then extracted with chloroform. The extract is dried with magnesium sulfate and the solvent is evaporated off. The resulting residue is purified by silica gel column chromatography (solvent: dichloromethane:methanol=50:1) to give 1-{1-[4-(5,6-dihydroxyhexyloxy)benzoyl]-4-piperidinyl]-3,4-dihydrocarbostyril (0.6 g).

Workup

  1. extractionextracted with chloroform
  2. dry with materialThe extract is dried with magnesium sulfate
  3. customthe solvent is evaporated off
  4. customThe resulting residue is purified by silica gel column chromatography (solvent: dichloromethane:methanol=50:1)

Sources & evidence

ORD record
ord-e46060b5f0444f93aa19f513f6ae193c
Source dataset
uspto-grants-1994_10
Patent number
US05356904

Reaction notes

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