1-(4-Pyridinyl)-4-piperidinecarbonyl chloride → 1-(2-Naphthylmethyl)-2-oxo-4-[1-(4-pyridyl)piperidin-4-ylcarbonyl]-piperazine

HRID 1976014Notes

Reaction equation

HRID 1976014 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][CH:10]([C:13](Cl)=[O:14])[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.FC(F)(F)C(O)=O.[CH:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][C:24]=1[CH2:33][N:34]1[CH2:39][CH2:38][NH:37][CH2:36][C:35]1=[O:40]>CN(C=O)C>[CH:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][C:24]=1[CH2:33][N:34]1[CH2:39][CH2:38][N:37]([C:13]([CH:10]2[CH2:11][CH2:12][N:7]([C:4]3[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=3)[CH2:8][CH2:9]2)=[O:14])[CH2:36][C:35]1=[O:40]

Participants

4

Reactant 2

HCID 111837001-(4-Pyridinyl)-4-piperidinecarbonyl chlorideHCID 227218291-(2-Naphthylmethyl)-2-oxopiperazine trifluoroacetate salt

Product 1

HCID 227217781-(2-Naphthylmethyl)-2-oxo-4-[1-(4-pyridyl)piperidin-4-ylcarbonyl]-piperazineYield 18%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Using an analogous procedure to that described in Example 1 except that DMF was used in place of methylene chloride as the reaction solvent, 1-(4-pyridyl)piperidine-4-carbonyl chloride was reacted with 1-(2-naphthylmethyl)-2-oxopiperazine trifluoroacetate salt to give 1-(2-naphthylmethyl)-2-oxo-4-[-(4-pyridyl)piperidin-4-ylcarbonyl]piperazine in 18% yield;

Sources & evidence

ORD record
ord-da36f2daa1bf4b60963d04dc4d10b2a3
Source dataset
uspto-grants-2001_05
Patent number
US06225309B1

Reaction notes

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