Formic Acid → 1-[[1,4-Dihydro-4-oxo-5-(phenylmethoxy)-1-(phenylmethyl)-2-pyridinyl]methyl]-2,3-piperazinedione

HRID 1252615Notes

Reaction equation

HRID 1252615 reaction equation
[O:1]=[C:2]1[C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][N:5]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:4]([CH2:23][N:24]2[CH2:29][CH2:28][N:27](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[C:26](=[O:49])[C:25]2=[O:50])=[CH:3]1.C(O)=O>ClCCl>[O:1]=[C:2]1[C:7]([O:8][CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:6][N:5]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:4]([CH2:23][N:24]2[CH2:29][CH2:28][NH:27][C:26](=[O:49])[C:25]2=[O:50])=[CH:3]1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 141824881-[[1,4-Dihydro-4-oxo-5-(phenylmethoxy)-1-(phenylmethyl)-2-pyridinyl]-methyl]-4-(triphenylmethyl)-2,3-piperazinedione

Product 1

HCID 141824891-[[1,4-Dihydro-4-oxo-5-(phenylmethoxy)-1-(phenylmethyl)-2-pyridinyl]methyl]-2,3-piperazinedioneYield 94.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[[1,4-dihydro-4-oxo-5-(phenylmethoxy)-1-(phenylmethyl)-2-pyridinyl]-methyl]-4-(triphenylmethyl)-2,3-piperazinedione (8.77 g, 13.23 mmol) in 65 ml of dichloromethane was added dropwise at room temperature 65 ml of formic acid. After stirring for three days, the volatiles were distilled off in vacuo and the residue triturated twice with ether to give 5.24 g of 1-[[1,4-dihydro-4-oxo-5-(phenylmethoxy)-1-(phenylmethyl)-2-pyridinyl]methyl]-2,3-piperazinedione, melting point 260°-265° C.

Workup

  1. distillationthe volatiles were distilled off in vacuo
  2. customthe residue triturated twice with ether

Sources & evidence

ORD record
ord-a91c1872c5394d02b9713ef531f835bd
Source dataset
uspto-grants-1988_05
Patent number
US04743685

Reaction notes

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