Hydrochloric Acid → HCID 15290688, compound

HRID 2257902Notes

Reaction equation

HRID 2257902 reaction equation
Cl.COC[O:5][CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][N:14]([CH2:22][CH2:23][CH2:24][CH2:25][O:26][C:27]2[CH:28]=[C:29]3[C:34](=[CH:35][CH:36]=2)[NH:33][C:32](=[O:37])[CH:31]=[CH:30]3)[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:8][CH2:7]1>CO>[OH:5][CH:6]1[CH2:7][CH2:8][N:9]([CH2:12][CH2:13][N:14]([CH2:22][CH2:23][CH2:24][CH2:25][O:26][C:27]2[CH:28]=[C:29]3[C:34](=[CH:35][CH:36]=2)[NH:33][C:32](=[O:37])[CH:31]=[CH:30]3)[CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 15290687HCID 15290687, compound

Product 1

HCID 15290688HCID 15290688, compoundYield 33.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

10 ml of 10% hydrochloric acid was added to a solution of 1.07 g of 6-[4-{N-[2-(4-methoxymethoxy-1-piperidinyl)ethyl]-N-benzylamino}butoxy]carbostyril in 10 ml of methanol. The mixture was stirred at room temperature for 1 day. The reaction mixture was washed with chloroform and then made alkaline with a 10% aqueous potassium hydroxide solution, followed by extraction with chloroform. The extract was washed with water and dried with magnesium sulfate. The solvent was removed by distillation. The resulting residue was purified by silica gel column chromatography (eluant: 5% methanol/chloroform), followed by recrystallization from ethyl acetate-diethyl ether, to obtain 330 mg of 6-[4-{N-[2-(4-hydroxy-1-piperidinyl)ethyl]-N-benzylamino}butoxy]-carbostyril.

Workup

  1. washThe reaction mixture was washed with chloroform
  2. extractionfollowed by extraction with chloroform
  3. washThe extract was washed with water
  4. dry with materialdried with magnesium sulfate
  5. customThe solvent was removed by distillation
  6. customThe resulting residue was purified by silica gel column chromatography (eluant: 5% methanol/chloroform)
  7. customfollowed by recrystallization from ethyl acetate-diethyl ether

Sources & evidence

ORD record
ord-665655cc6b9740cfa7ff34bd063be4b1
Source dataset
uspto-grants-1997_08
Patent number
US05658926

Reaction notes

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