Hydrazine hydrate (1:1) → HCID 9804945, compound

HRID 1296590Notes

Reaction equation

HRID 1296590 reaction equation
[CH2:1]([C:8]1[N:16]([CH2:17][CH2:18][NH:19][CH2:20][CH3:21])[C:15]2[C:14](=[O:22])[N:13]([CH2:23][CH2:24][CH3:25])[C:12](=[O:26])[N:11]([CH2:27][CH2:28][C:29]3[CH:34]=[CH:33][C:32]([N+:35]([O-])=O)=[CH:31][CH:30]=3)[C:10]=2[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN.[H][H]>[Pd]>[NH2:35][C:32]1[CH:31]=[CH:30][C:29]([CH2:28][CH2:27][N:11]2[C:10]3[N:9]=[C:8]([CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[N:16]([CH2:17][CH2:18][NH:19][CH2:20][CH3:21])[C:15]=3[C:14](=[O:22])[N:13]([CH2:23][CH2:24][CH3:25])[C:12]2=[O:26])=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 66995936HCID 66995936, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 9804945HCID 9804945, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

By the method of Example 3, 8-benzyl-3-[2-(4-nitrophenyl)ethyl]-1-propylxanthine, is reacted with sodium carbonate, 1,2-dichloroethane and ethylamine to yield 8-benzyl-7-(2-ethylamino)ethyl-3-[2-(4-nitrophenyl)ethyl]-1-propylxanthine. By the method of Example 4, 8-benzyl-7-(2-ethylamino)ethyl-3-[2-(4-nitrophenyl)ethyl]-1-propylxanthine is reduced with hydrazine hydrate or hydrogen gas in the presence of a palladium catalyst to yield 3-[2-(4-aminophenyl)ethyl]-8-benzyl-7-(2-ethylamino)ethyl-1-propylxanthine free base. The corresponding dihydrochloride salt is then made on exposure to an excess of hydrogen chloride in solution.

Sources & evidence

ORD record
ord-84782fde173e4890aa8bb745968212d2
Source dataset
uspto-grants-2007_07
Patent number
US07247639B2

Reaction notes

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