Diethyl squarate → HCID 18914179, compound

HRID 1292354Notes

Reaction equation

HRID 1292354 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH:6]=[CH:5][C:4]=1[CH2:16][C:17]([N:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[CH3:31])[CH2:21][CH:20]1[C:32]([NH2:34])=[O:33])=[O:18].[CH2:35]([O:37][C:38]1[C:39](=O)[C:40](=[O:45])[C:41]=1[O:42]CC)[CH3:36]>C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH:10]2[CH2:15][CH2:14][N:13]([C:39]3[C:40](=[O:45])[C:41](=[O:42])[C:38]=3[O:37][CH2:35][CH3:36])[CH2:12][CH2:11]2)[CH:6]=[CH:5][C:4]=1[CH2:16][C:17]([N:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[CH3:31])[CH2:21][CH:20]1[C:32]([NH2:34])=[O:33])=[O:18]

Participants

4

Reactant 2

HCID 123228Diethyl squarateHCID 54376204HCID 54376204, compound

Product 1

HCID 18914179HCID 18914179, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(2-Methoxy-4-(4-piperidyloxy)phenylacetyl)-4-(2-methylphenyl) piperazine-2-carboxamide (128 mg, 0.274 mmole) was dissolved in 4 ml of absolute ethanol. 3,4-Diethoxy-3-cyclobutene-1,2-dione (62 mg, 0.364 mmole), prepared according to the procedure in Angew. Chem. Int. Ed. 1966, 5(10), 890, was then added to the solution and the resulting reaction mixture was heated to reflux for 72 hr. The reaction mixture was cooled and filtered. The filter cake was washed with cold ethanol and dried to give the title compound as a white solid: m.p. 155°-157° C.

Workup

  1. addition1966, 5(10), 890, was then added to the solution
  2. customthe resulting reaction mixture
  3. temperaturewas heated
  4. temperatureto reflux for 72 hr
  5. temperatureThe reaction mixture was cooled
  6. filtrationfiltered
  7. washThe filter cake was washed with cold ethanol
  8. customdried

Sources & evidence

ORD record
ord-1b662ce2b3eb4e65ba009451e1c85473
Source dataset
uspto-grants-1998_05
Patent number
US05756504

Reaction notes

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