Dichloromethane → HCID 131715729, compound

HRID 868335Notes

Reaction equation

HRID 868335 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=[C:8]([CH2:12][CH3:13])[C:9]([OH:11])=[O:10])[CH:2]=1.[C:14]1([CH:20]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:21]2[CH2:26][CH2:25][N:24]([CH2:27][CH2:28][CH2:29][CH2:30][NH2:31])[CH2:23][CH2:22]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl.C(N=C=NCCCN(C)C)C.ClCCl.[C:53]([OH:60])(=[O:59])/[CH:54]=[CH:55]/[C:56]([OH:58])=[O:57]>C(O)C.C(OCC)C>[C:53]([OH:60])(=[O:59])/[CH:54]=[CH:55]/[C:56]([OH:58])=[O:57].[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=[C:8]([CH2:12][CH3:13])[C:9]([NH:31][CH2:30][CH2:29][CH2:28][CH2:27][N:24]2[CH2:25][CH2:26][N:21]([CH:20]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:22][CH2:23]2)=[O:11])[CH:2]=1.[C:53]([OH:60])(=[O:59])/[CH:54]=[CH:55]/[C:56]([OH:58])=[O:57].[C:53]([OH:60])(=[O:59])/[CH:54]=[CH:55]/[C:56]([OH:58])=[O:57].[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=[C:8]([CH2:12][CH3:13])[C:9]([NH:31][CH2:30][CH2:29][CH2:28][CH2:27][N:24]2[CH2:23][CH2:22][N:21]([CH:20]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH2:26][CH2:25]2)=[O:10])[CH:2]=1

Participants

8

Reactant 5

HCID 6344DichloromethaneHCID 444972Fumaric AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 139569931-(4-Aminobutyl)-4-(diphenylmethyl)piperazineHCID 539035433-(3-Pyridyl)-2-ethylacrylic acid

Product 1

HCID 131715729HCID 131715729, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 0.8 g of 3-(3-pyridyl)-2-ethylacrylic acid, 2.2 g of 4-(4-diphenylmethyl-1-piperazinyl)butylamine, 0.87 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, and 30 ml of dichloromethane is stirred at room temperature overnight. The reaction mixture is washed with water and dried over magnesium sulfate, and the solvent is distilled off. The residue is chromatographed on silica gel with chloroform-methanol (30:1) to give a brown oil, which is dissolved in 5 ml of ethanol containing 1.0 g of fumaric acid. To the resulting solution is added 15 ml of diethyl ether, and the solid separated is collected to give 1.4 g of the title compound. m.p. 137°-141° C. (recrystallized from ethanol-diethyl ether)

Workup

  1. washThe reaction mixture is washed with water
  2. dry with materialdried over magnesium sulfate
  3. distillationthe solvent is distilled off
  4. customThe residue is chromatographed on silica gel with chloroform-methanol (30:1)
  5. customto give a brown oil, which
  6. customthe solid separated
  7. customis collected

Sources & evidence

ORD record
ord-09e7cd61eafe4904b53e2d065c232034
Source dataset
uspto-grants-1988_10
Patent number
US04778796

Reaction notes

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