Benzaldehyde → HCID 69132355, compound

HRID 2370053Notes

Reaction equation

HRID 2370053 reaction equation
C([N:4]1[CH2:9][C:8](=[O:10])[NH:7][C:6](=[CH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:14][N:13]=2)[C:5]1=[O:26])(=O)C.[CH:27](=O)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[CH2:35](N(CC)CC)C>CN(C)C=O>[CH2:19]([O:18][C:15]1[CH:16]=[CH:17][C:12]([CH:11]=[C:6]2[NH:7][C:8](=[O:10])[C:9](=[CH:35][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[NH:4][C:5]2=[O:26])=[N:13][CH:14]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 8471TriethylamineHCID 400200HCID 400200, compound

Product 1

HCID 69132355HCID 69132355, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Compound A (3.51 g) was added to a 40 mL of dimethylformamide solution containing benzaldehyde (1 eq.) and 4 equivalents of triethylamine (4 eq.). The solution was refluxed at 60° C. for 16 hr and cooled at an ice bath to produce a yellow precipitate. The precipitate was then collected and washed with ethyl acetate to give 3.3 g (83%) of 3-[(5-benzyloxypyridin-2-yl)methylidene]-6-(benzylmethylidene)piperazine-2,5-dione (Compound B). mp: 223-225° C.; 1H-NMR (400 MHz, DMSO): 5.243 (s, 2H), 6.695 (s, 1H), 6.812 (s, 1H), 7.346-7.634 (m, 12H, aromatic), 8.528 (s, 1H), 10.245 (s, 1H), and 12.289 (s, 1H).

Workup

  1. temperaturecooled at an ice bath
  2. customto produce a yellow precipitate
  3. customThe precipitate was then collected
  4. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-600391d7883640ba936be18f46b87900
Source dataset
uspto-grants-2014_04
Patent number
US08710062B2

Reaction notes

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