Sodium hydride → 1-[[1,4-Dihydro-4-oxo-5-(phenylmethoxy)-1-(phenylmethyl)-2-pyridinyl]-methyl]-4-(triphenylmethyl)-2,3-piperazinedione

HRID 1252614Notes

Reaction equation

HRID 1252614 reaction equation
[C:1]1([C:7]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:8]2[CH2:13][CH2:12][NH:11][C:10](=[O:14])[C:9]2=[O:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[H][H].Cl[CH2:33][C:34]1[N:35]([CH2:49][C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[CH:36]=[C:37]([O:41][CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[C:38](=[O:40])[CH:39]=1>CN(C)C=O>[O:40]=[C:38]1[C:37]([O:41][CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[CH:36][N:35]([CH2:49][C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[C:34]([CH2:33][N:11]2[CH2:12][CH2:13][N:8]([C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:9](=[O:15])[C:10]2=[O:14])=[CH:39]1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 141824862-(chloromethyl)-5-(phenylmethoxy)-1-(phenylmethyl)-4(1H)-pyridinoneHCID 14182487N-(Triphenylmethyl)piperazine-2,3-dioneHCID 178418361HCID 178418361, compound

Product 1

HCID 141824881-[[1,4-Dihydro-4-oxo-5-(phenylmethoxy)-1-(phenylmethyl)-2-pyridinyl]-methyl]-4-(triphenylmethyl)-2,3-piperazinedioneYield 66.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of N-(triphenylmethyl)piperazine-2,3-dione (4.19 g, 11.77 mmol) in 95 ml of dry dimethylformamide was added 0.35 g (11.77 mmol) of sodium hydride (80% oil). After the hydrogen evolution had ceased, a solution of 2-(chloromethyl)-5-(phenylmethoxy)-1-(phenylmethyl)-4(1H)-pyridinone (4.0 g, 11.77 mmol) in 25 ml of dry dimethylformamide was added to the thick suspension which then turned into a clear solution. After one hour of stirring at room temperature, precipitation started. After two hours, the crystals were filtered off, washed and dried in vacuo, yielding 5.13 g of the title compound, melting point 165°-168° C.

Workup

  1. customprecipitation
  2. waitAfter two hours
  3. filtrationthe crystals were filtered off
  4. washwashed
  5. customdried in vacuo

Sources & evidence

ORD record
ord-0c6904bbc892463dbc8d3c7b28448abb
Source dataset
uspto-grants-1988_05
Patent number
US04743685

Reaction notes

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