Fumaric Acid → HCID 86744795, compound

HRID 2051402Notes

Reaction equation

HRID 2051402 reaction equation
[OH:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5](/[CH:10]=[CH:11]/[CH:12]=[CH:13]/[C:14]([NH:16][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][CH:22]([C:25]3[C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[NH:27][CH:26]=3)[CH2:21][CH2:20]2)=[O:15])=[CH:4][C:3]=1[O:34][CH3:35].[C:36]([OH:43])(=[O:42])/[CH:37]=[CH:38]/[C:39]([OH:41])=[O:40]>CO>[C:36]([OH:43])(=[O:42])/[CH:37]=[CH:38]/[C:39]([OH:41])=[O:40].[OH:1][C:2]1[C:3]([O:34][CH3:35])=[CH:4][C:5](/[CH:10]=[CH:11]/[CH:12]=[CH:13]/[C:14]([NH:16][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][CH:22]([C:25]3[C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[NH:27][CH:26]=3)[CH2:21][CH2:20]2)=[O:15])=[CH:6][C:7]=1[O:8][CH3:9]

Participants

4

Reactant 2

HCID 444972Fumaric AcidHCID 10412674HCID 10412674, compound

Product 1

HCID 86744795HCID 86744795, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-[2-{5-(4-hydroxy-3, 5-dimethoxyphenyl)-(2E, 4E)-2, 4-pentadienoylamino}ethyl]-4-(3-indolyl)-piperidine (7.0 g), fumaric acid (1.708 g) and methanol (200 ml) was refluxed. After the solid was completely dissolved, the mixture was filtered and the filtrate was allowed to stand at ambient temperature. The resulting precipitate was collected by filtration, washed with methanol (10 ml) and dried to give 1-[2-{5-(4-hydroxy-3, 5-dimethoxyphenyl)-(2E, 4E)-2, 4-pentadienoylamino}ethyl]-4-(3-indolyl)piperidine fumarate (7.58 g).

Workup

  1. temperaturewas refluxed
  2. dissolutionAfter the solid was completely dissolved
  3. filtrationthe mixture was filtered
  4. customto stand at ambient temperature
  5. filtrationThe resulting precipitate was collected by filtration
  6. washwashed with methanol (10 ml)
  7. customdried

Sources & evidence

ORD record
ord-d043b724cc7e4bdca7f55faea49f4b79
Source dataset
uspto-grants-1991_05
Patent number
US05017703

Reaction notes

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