1-Pyrrolidinepropanamine → 6-[3-(1-Pyrrolidinyl)propylamino]-7,8,9,10-tetrahydro-1,2,4-triazolo[3,4-a]phthalazine
Reaction equation
Cl[C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[C:5]2=[N:12][N:13]=[CH:14][N:4]2[N:3]=1.[NH2:15][CH2:16][CH2:17][CH2:18][N:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1>>[N:19]1([CH2:18][CH2:17][CH2:16][NH:15][C:2]2[C:11]3[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=3[C:5]3=[N:12][N:13]=[CH:14][N:4]3[N:3]=2)[CH2:23][CH2:22][CH2:21][CH2:20]1Participants
3
Procedure
A solution of 5.0 g of 6-chloro-7,8,9,10-tetrahydro-1,2,4-triazolo[3,4-a]phthalazine in 25 ml of 1-(3-aminopropyl)pyrrolidine was heated at reflux for 15 hours. Excess amine was removed by distillation and the resulting residue was partitioned between methylene chloride and saturated aqueous sodium bicarbonate solution. The organic layer was separated, dried over sodium sulfate and concentrated. The brown residue obtained was triturated with ether and the resulting solid was recrystallized from toluene to give 6-[3-(1-pyrrolidinyl)propylamino]-7,8,9,10-tetrahydro-1,2,4-triazolo[3,4-a]phthalazine melting at about 169°-171° C.
Workup
- temperatureat reflux for 15 hours
- customExcess amine was removed by distillation
- customthe resulting residue was partitioned between methylene chloride and saturated aqueous sodium bicarbonate solution
- customThe organic layer was separated
- dry with materialdried over sodium sulfate
- concentrationconcentrated
- customThe brown residue obtained
- customwas triturated with ether
- customthe resulting solid was recrystallized from toluene
Sources & evidence
- ORD record
- ord-d6168d9d63a5491687d6a7afcb15ab96
- Source dataset
- uspto-grants-1984_12
- Patent number
- US04487930
Reaction notes
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