Formaldehyde → 4-(4-Methylsulfonylaminobenzoyl)-1-[2-(2-quinoxalinyl)ethyl]piperidine

HRID 1646205Notes

Reaction equation

HRID 1646205 reaction equation
Cl.[CH3:2][S:3]([NH:6][C:7]1[CH:20]=[CH:19][C:10]([C:11]([CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[O:12])=[CH:9][CH:8]=1)(=[O:5])=[O:4].[CH3:21][C:22]1[CH:31]=[N:30][C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:23]=1.[CH2:32]=O.[OH-].[Na+]>C(O)C>[CH3:2][S:3]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([C:11]([CH:13]2[CH2:18][CH2:17][N:16]([CH2:32][CH2:21][C:22]3[CH:31]=[N:30][C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[N:23]=3)[CH2:15][CH2:14]2)=[O:12])=[CH:19][CH:20]=1)(=[O:4])=[O:5]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 236862-MethylquinoxalineHCID 14130042N-[4-(piperidine-4-carbonyl)-phenyl]methanesulfonamide hydrochloride

Product 1

HCID 141300554-(4-Methylsulfonylaminobenzoyl)-1-[2-(2-quinoxalinyl)ethyl]piperidineYield 5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

5.0 g (15.7 mmol) of 4-(4-methylsulfonylaminobenzoyl)piperidine hydrochloride was suspended in 5 ml of ethanol. 2.49 g of 2-methylquinoxaline and 7.0 ml of formalin were added to the suspension and the mixture was stirred at 90° C. for 1 h. After cooling, the mixture was neutralized with a 20% aqueous sodium hydroxide solution and the formed crystals were recrystallized from ethyl acetate to obtain 0.32 g (yield: 5%) of the intended compound.

Workup

  1. temperatureAfter cooling
  2. customthe formed crystals were recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-1351bd025f674070a8c2b994ae68b40f
Source dataset
uspto-grants-1993_01
Patent number
US05179095

Reaction notes

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