1,4'-Bipiperidine → 3,5-Dimethyl-2-[4-[4-[2-(4-piperidinopiperidino)-ethoxy]benzoyl]benzylthio]-4(3H)-quinazolinone dihydrochloride

HRID 1291379Notes

Reaction equation

HRID 1291379 reaction equation
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:33]=[CH:32][C:8]([C:9]([C:11]2[CH:31]=[CH:30][C:14]([CH2:15][S:16][C:17]3[N:26]([CH3:27])[C:25](=[O:28])[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][C:23]=4[CH3:29])[N:18]=3)=[CH:13][CH:12]=2)=[O:10])=[CH:7][CH:6]=1.[N:34]1([CH:40]2[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]2)[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1>CN(C=O)C>[ClH:1].[ClH:1].[CH3:27][N:26]1[C:25](=[O:28])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][C:23]=2[CH3:29])[N:18]=[C:17]1[S:16][CH2:15][C:14]1[CH:30]=[CH:31][C:11]([C:9](=[O:10])[C:8]2[CH:32]=[CH:33][C:5]([O:4][CH2:3][CH2:2][N:43]3[CH2:44][CH2:45][CH:40]([N:34]4[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]4)[CH2:41][CH2:42]3)=[CH:6][CH:7]=2)=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 786071,4'-BipiperidineHCID 189188132-[4-[4-(2-Chloroethoxy)benzoyl]benzylthio]-3,5-dimethyl-4(3H)-quinazolinone

Product 1

HCID 189192323,5-Dimethyl-2-[4-[4-[2-(4-piperidinopiperidino)-ethoxy]benzoyl]benzylthio]-4(3H)-quinazolinone dihydrochlorideYield 137.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-[4-[4-(2-chloroethoxy)benzoyl]benzylthio]-3,5-dimethyl-4(3H)-quinazolinone (375 mg) and 4-piperidinopiperidine (434 mg) in DMF (5 ml) was stirred at 100° C. for 7 hours. This reaction mixture was concentrated and the residue was dissolved in ethyl acetate, washed with water, dried, and concentrated. Then, hydrogen chloride/ethyl acetate was added and the precipitated hydrochloride was recovered by filtration and dried to provide the title compound as colorless solid (368 mg).

Workup

  1. concentrationThis reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated
  6. additionThen, hydrogen chloride/ethyl acetate was added
  7. filtrationthe precipitated hydrochloride was recovered by filtration
  8. customdried

Sources & evidence

ORD record
ord-449dd8d14ef349439cf551a2e47c5cf0
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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