Hydrochloric Acid → HCID 14747684, compound

HRID 1609503Notes

Reaction equation

HRID 1609503 reaction equation
COC[O:4][CH:5]1[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][N:13]([CH2:32][CH:33]2[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]2)[C:14]([CH2:16][CH2:17][CH2:18][CH2:19][O:20][C:21]2[CH:22]=[C:23]3[C:28](=[CH:29][CH:30]=2)[NH:27][C:26](=[O:31])[CH:25]=[CH:24]3)=[O:15])[CH2:7][CH2:6]1.Cl.[OH-].[K+]>CO>[OH:4][CH:5]1[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][N:13]([CH2:32][CH:33]2[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]2)[C:14]([CH2:16][CH2:17][CH2:18][CH2:19][O:20][C:21]2[CH:22]=[C:23]3[C:28](=[CH:29][CH:30]=2)[NH:27][C:26](=[O:31])[CH:25]=[CH:24]3)=[O:15])[CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 14747741HCID 14747741, compound

Product 1

HCID 14747684HCID 14747684, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 30 ml of methanol is dissolved 12.10 g of 6-{4-[N-(4-methoxymethoxy-1-piperidinyl)ethyl-N-cyclooctylmethylaminocarbonyl]butoxy}carbostyril. Thereto is added 240 ml of 5% hydrochloric acid. The mixture is stirred for 8 hours at room temperature. To the mixture is added with a 10% aqueous potassium hydroxide solution under ice cooling to make the mixture alkaline. The resulting mixture is extracted with methylene chloride. The extract is washed with water and dried with anhydrous magnesium sulfate. The solvent is removed by evaporation. The residue is purified by means of a silica gel column chromatography (eluant; chloroform:methanol=8:1) and recyrstallized from ethanol to obtain 6.50 g of 6-{4-[N-(4-hydroxy-1-piperidinyl)ethyl-N-cyclooctylmethylaminocarbonyl]butoxy}carbostyril.

Workup

  1. extractionThe resulting mixture is extracted with methylene chloride
  2. washThe extract is washed with water
  3. dry with materialdried with anhydrous magnesium sulfate
  4. customThe solvent is removed by evaporation
  5. customThe residue is purified by means of a silica gel column chromatography (eluant; chloroform:methanol=8:1)

Sources & evidence

ORD record
ord-e9c15c5d54574af089f2f855a362a71a
Source dataset
uspto-grants-1995_03
Patent number
US05401740

Reaction notes

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