Hydrochloric Acid → N-(5-ethylpyrimidin-4-yl)-4-[3-(1-benzylpiperidin-4-yl)propanoyl]aniline

HRID 976129Notes

Reaction equation

HRID 976129 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][C:16]([C:18]2[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=2)=[O:17])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:26]1[C:31]([CH2:32][CH3:33])=[CH:30][N:29]=[CH:28][N:27]=1.Cl.C[O-].[Na+].CO>C(O)C>[CH2:32]([C:31]1[C:26]([NH:22][C:21]2[CH:20]=[CH:19][C:18]([C:16](=[O:17])[CH2:15][CH2:14][CH:11]3[CH2:12][CH2:13][N:8]([CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[CH2:9][CH2:10]3)=[CH:24][CH:23]=2)=[N:27][CH:28]=[N:29][CH:30]=1)[CH3:33]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 199689164-Chloro-5-ethylpyrimidineHCID 199689194-[3-(1-Benzylpiperidin-4-yl)propanoyl]anilineHCID 23694274Sodium methanolate methanol

Product 1

HCID 19968894N-(5-ethylpyrimidin-4-yl)-4-[3-(1-benzylpiperidin-4-yl)propanoyl]anilineYield 58.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To 10 ml of ethanol were added 0.23 g of 4-[3-(1-benzylpiperidin-4-yl)propanoyl]aniline and 0.13 g of 4-chloro-5-ethylpyrimidine, and after adding 2 ml of an ethanol solution of hydrochloric acid (containing 0.071 g of hydrochloric acid), the mixture was reacted under reflux for 2 hours. After cooling, a 28% sodium methylate-methanol solution was added to the reaction mixture to make it alkaline, and then the mixture was condensed under reduced pressure. The obtained residue was applied to silica gel column chromatography to obtain 0.18 g of the title compound as pale yellow crystal.

Workup

  1. customthe mixture was reacted
  2. temperatureunder reflux for 2 hours
  3. temperatureAfter cooling
  4. customcondensed under reduced pressure

Sources & evidence

ORD record
ord-fc8d77730ea844e4a41c0bd46b991193
Source dataset
uspto-grants-1997_03
Patent number
US05610303

Reaction notes

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