7-[(5-Chloromethyl-1,2,4-oxadiazol-3-yl)-methyl]-theophylline → 7-[(5-Aminomethyl-1,2,4-oxadiazol-3-yl)-methyl]-theophylline-hydrochloride

HRID 1285166Notes

Reaction equation

HRID 1285166 reaction equation
[Cl:1][CH2:2][C:3]1[O:7][N:6]=[C:5]([CH2:8][N:9]2[C:18]3[C:17](=[O:19])[N:15]([CH3:16])[C:14](=[O:20])[N:13]([CH3:21])[C:12]=3[N:11]=[CH:10]2)[N:4]=1.C(N)(=O)C1C(=CC=CC=1)C([NH2:27])=O.[K]>CN(C)C=O>[ClH:1].[NH2:27][CH2:2][C:3]1[O:7][N:6]=[C:5]([CH2:8][N:9]2[C:18]3[C:17](=[O:19])[N:15]([CH3:16])[C:14](=[O:20])[N:13]([CH3:21])[C:12]=3[N:11]=[CH:10]2)[N:4]=1

Participants

4

Reactant 2

HCID 202498997-[(5-Chloromethyl-1,2,4-oxadiazol-3-yl)-methyl]-theophyllineHCID 53445390Potassium phthalamide

Product 1

HCID 202499927-[(5-Aminomethyl-1,2,4-oxadiazol-3-yl)-methyl]-theophylline-hydrochlorideYield 74.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

30.9 g. 7-[(5-chloromethyl-1,2,4-oxadiazol-3-yl)-methyl]-theophylline are heated in 300 cm3 dimethylformamide with 18.5 g. potassium phthalamide under stirring for 6 hours. Dimethylformamide is distilled off at reduced pressure, and the residue is triturated with 300 cm3 ethanol and 5.2 g. of hydrazine hydrate are added, the mixture is heated on water bath for 2 hours, acidified with concentrated aqueous hydrochloric acid, the mixture is boiled and filtered when hot and the filtrate is evaporated. After crystallization from methanol 24.7 g. (74.2% yield) of 7-[(5-aminomethyl-1,2,4-oxadiazol-3-yl)-methyl]-theophylline-hydrochloride are obtained, m.p.: 204°-207° C.

Workup

  1. distillationDimethylformamide is distilled off at reduced pressure
  2. customthe residue is triturated with 300 cm3 ethanol and 5.2 g
  3. additionof hydrazine hydrate are added
  4. temperaturethe mixture is heated on water bath for 2 hours
  5. filtrationfiltered when hot
  6. customthe filtrate is evaporated
  7. customAfter crystallization from methanol 24.7 g

Sources & evidence

ORD record
ord-e1c804aa175a4d829526cdfcfcb3497a
Source dataset
uspto-grants-1986_01
Patent number
US04565817

Reaction notes

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