1-Pyrrolidineethanamine → 6-[2-(1-Pyrrolidinyl)ethylamino]-7,8,9,10-tetrahydro-1,2,4-triazolo[3,4-a]phthalazine

HRID 1154014Notes

Reaction equation

HRID 1154014 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][N:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1>COCCO>[N:18]1([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)[CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 13441-PyrrolidineethanamineHCID 126224416-Chloro-7,8,9,10-tetrahydro-[1,2,4]triazolo[3,4-a]phthalazine

Product 1

HCID 133655886-[2-(1-Pyrrolidinyl)ethylamino]-7,8,9,10-tetrahydro-1,2,4-triazolo[3,4-a]phthalazine

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

A solution of 5.0 g of 6-chloro-7,8,9,10-tetrahydro-1,2,4-triazolo[3,4-a]phthalazine and 10.0 g of 1-(2-aminoethyl)pyrrolidine in 50 ml of 2-methoxyethanol was heated at reflux for 15 hours. The solution was then concentrated 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 concentrate was triturated with ether and the solid which formed was separated by filtration to give 6-[2-(1-pyrrolidinyl)ethylamino]-7,8,9,10-tetrahydro-1,2,4-triazolo[3,4-a]phthalazine melting at about 160°-162° C. after recrystallization from a mixture of toluene and hexane. This compound has the following structural formula ##STR3##

Workup

  1. temperatureat reflux for 15 hours
  2. concentrationThe solution was then concentrated
  3. customthe resulting residue was partitioned between methylene chloride and saturated aqueous sodium bicarbonate solution
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe concentrate was triturated with ether
  8. customthe solid which formed
  9. customwas separated by filtration

Sources & evidence

ORD record
ord-dde6ebfad6b342e69b42e8d97b5b3168
Source dataset
uspto-grants-1984_12
Patent number
US04487930

Reaction notes

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