Potassium Carbonate → 1-[1-{4-[5-(4-Amino-1-piperidinyl)pentoyloxy]benzoyl}-4-piperidinyl]-3,4-dihydrocarbostyril

HRID 1708318Notes

Reaction equation

HRID 1708318 reaction equation
FC(F)(F)C(NC1CCN(CCCCCO[C:18]2[CH:42]=[CH:41][C:21]([C:22]([N:24]3[CH2:29][CH2:28][CH:27]([N:30]4[C:40]5[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=5)[CH2:34][CH2:33][C:31]4=[O:32])[CH2:26][CH2:25]3)=[O:23])=[CH:20][CH:19]=2)CC1)=O.[C:45](=[O:48])([O-])[O-:46].[K+].[K+]>CO>[NH2:30][CH:27]1[CH2:28][CH2:29][N:24]([CH2:22][CH2:21][CH2:20][CH2:19][C:45]([O:46][C:18]2[CH:42]=[CH:41][C:21]([C:22]([N:24]3[CH2:25][CH2:26][CH:27]([N:30]4[C:40]5[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=5)[CH2:34][CH2:33][C:31]4=[O:32])[CH2:28][CH2:29]3)=[O:23])=[CH:20][CH:19]=2)=[O:48])[CH2:25][CH2:26]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 189607451-[1-{4-[5-(4-Trifluoroacetylamino-1-piperidinyl)pentyloxy]benzoyl}-4-piperidinyl]-3,4-dihydrocarbostyril

Product 1

HCID 572403741-[1-{4-[5-(4-Amino-1-piperidinyl)pentoyloxy]benzoyl}-4-piperidinyl]-3,4-dihydrocarbostyrilYield 128.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-[1-{4-[5-(4-Trifluoroacetylamino-1-piperidinyl)pentyloxy]benzoyl}-4-piperidinyl]-3,4-dihydrocarbostyril (1.8 g) is dissolved in methanol (40 ml), and thereto is added potassium carbonate (0.8 g). The mixture is stirred at room temperature overnight. The reaction solution is concentrated and thereto is added water. The mixture is extracted with chloroform, dried over sodium carbonate, and purified by silica gel column chromatography (eluent; dichloromethane:methanol=10:1) to give 1-[1-{4-[5-(4-amino-1-piperidinyl)pentoyloxy]benzoyl}-4-piperidinyl]-3,4-dihydrocarbostyril (1 g) as colorless oil.

Workup

  1. concentrationThe reaction solution is concentrated
  2. additionis added water
  3. extractionThe mixture is extracted with chloroform
  4. dry with materialdried over sodium carbonate
  5. custompurified by silica gel column chromatography (eluent; dichloromethane:methanol=10:1)

Sources & evidence

ORD record
ord-438adee7253744efbbc261e97762f74d
Source dataset
uspto-grants-1994_10
Patent number
US05356904

Reaction notes

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