1-Aminopyrrole → HCID 20263906, compound
Reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1.[NH2:15][N:16]1[CH:20]=[CH:19][CH:18]=[CH:17]1.[BH4-].[Na+]>C1C=CC=CC=1>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][CH:11]([NH:15][N:16]2[CH:20]=[CH:19][CH:18]=[CH:17]2)[CH2:10][CH2:9]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
A solution of 1-(2-thienylethyl)-4-piperidone (24.6 g, 0.12 mole) and 1-aminopyrrole (12 g, 0.15 mole) in 200 ml of benzene was stirred at reflux for 4 hours. The resultant mixture was cooled and evaporated to an oil which in turn was dissolved in 200 ml of isopropanol and 50 ml of methanol. To the resultant solution was added NaBH4 (9.1 g, 0.24 mole). The mixture was stirred at 80° C. for 2 hours, cooled, evaporated, stirred with water and then extracted with ethyl acetate-ether. The organic extract was washed twice with water and saturated NaCl solution and was dried (anhydrous MgSO4), filtered and evaporated to 33 g of an oil of 1-[2-(2-thienyl)ethyl]-4-(1H-pyrrol-1-yl)aminopiperidine.
Workup
- temperatureat reflux for 4 hours
- customevaporated to an oil which in turn
- dissolutionwas dissolved in 200 ml of isopropanol
- temperaturecooled
- customevaporated
- stirringstirred with water
- extractionextracted with ethyl acetate-ether
- extractionThe organic extract
- washwas washed twice with water and saturated NaCl solution
- dry with materialwas dried (anhydrous MgSO4)
- filtrationfiltered
- customevaporated to 33 g of an oil of 1-[2-(2-thienyl)ethyl]-4-(1H-pyrrol-1-yl)aminopiperidine
Sources & evidence
- ORD record
- ord-409e62bd6453487799840a07acd9695a
- Source dataset
- uspto-grants-1984_06
- Patent number
- US04452803
Reaction notes
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