Oxalic Acid → HCID 14810850, compound

HRID 1710098Notes

Reaction equation

HRID 1710098 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[N:15]=[C:14]([CH:16]=[CH2:17])[O:13][N:12]=2)=[CH:3]1.[NH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.[C:24]([OH:29])(=[O:28])[C:25]([OH:27])=[O:26]>C(O)C.ClCCl>[C:24]([OH:29])(=[O:28])[C:25]([OH:27])=[O:26].[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[N:15]=[C:14]([CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)[O:13][N:12]=2)=[CH:3]1

Participants

6

Reactant 3

HCID 971Oxalic AcidHCID 8082PiperidineHCID 14773942HCID 14773942, compound

Product 1

HCID 14810850HCID 14810850, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

2[3-(1-Methylindol-3-yl)-1,2,4-oxadiazol-5-yl]ethene (0.4 g) was partially dissolved in ethanol. Piperidine (2 ml) was added to the mixture and this was stirred for 10 minutes. Ethanol was evaporated under reduced pressure and excess piperidine was removed by heating under high vacuum. The residual oil crystallised upon refrigeration. The crude oil was converted to the monooxalate salt by treatment with 1 equivalent of oxalic acid in dichloromethane which afforded a white amorphous powder. This was recrystallised from ethanol yielding the title compound, m.p. 186°-188° C. Found: C, 59.85; H, 6.10; N, 13.95; C18H22N4O. (COOH)2 requires C, 59.99; H, 6.04; N, 13.99%; δH (360 MHz, D2O) 1.48-2.06 (8H, m, CH2 pip: NCH2CH2 ×2+NCH2CH2CH2), 3.00-3.08 (2H, m, NCH2) 3.50 (2H, t, J=9 Hz, CH2CH2N), 3.58-3.70 (4H, m, CH2CH2N+NCH2CH2 pip, overlapping), 3.87 (3H, s, NCH3), 7.36 (dt, 1H, J=7.2, 1.1 Hz, H-5 or H-6), 7.42 (1H, d, J=7.2, 1.1 Hz, H-5 or H-6) 7.58 (1H, d, J=8.2 Hz, H-7), 7.89 (s, 1H, H-2), 8.00 (1H, d, J=7.5 Hz, H-4); m/z (CI+) 311 (M+ +1, 100%), 226 (30), 157 (70), 98 (90).

Workup

  1. customEthanol was evaporated under reduced pressure and excess piperidine
  2. customwas removed
  3. temperatureby heating under high vacuum
  4. customThe residual oil crystallised upon refrigeration
  5. customafforded a white amorphous powder
  6. customThis was recrystallised from ethanol yielding the title compound, m.p. 186°-188° C

Sources & evidence

ORD record
ord-d20d6bd56dbb4877b7564ee6df2817f4
Source dataset
uspto-grants-1990_08
Patent number
US04952587

Reaction notes

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