Hydrochloric Acid → 5-(2-Dimethylamino-ethyl)-3-methyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-one
Reaction equation
C([O:3][C:4]([C:6]1[C:10]([CH3:11])=[CH:9][NH:8][C:7]=1[CH2:12][CH2:13][NH:14][CH2:15][CH2:16][N:17]([CH3:19])[CH3:18])=O)C.C[Al](C)C.Cl.[OH-].[Na+]>C1(C)C=CC=CC=1.O>[CH3:18][N:17]([CH3:19])[CH2:16][CH2:15][N:14]1[CH2:13][CH2:12][C:7]2[NH:8][CH:9]=[C:10]([CH3:11])[C:6]=2[C:4]1=[O:3]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A stirred solution of 2-[2-(2-dimethylamino-ethylamino)-ethyl]-4-methyl-1H-pyrrole-3-carboxylic acid ethyl ester (267 mg, 1 mmol) in 5 ml of toluene was added dropwise with 2M trimethyl aluminum in toluene (1 ml, 2 mmol) under an argon atmosphere. The mixture was stirred for 1 hour at room temperature and heated to reflux for another 4 hours. The reaction mixture was cooled down to 0° C. in an ice-water bath, added with 1N hydrochloric acid (10 ml) and cold water (10 ml). The mixture was adjusted to pH12 with 10% aqueous sodium hydroxide solution and extracted with dichloromethane (25 ml×5). The combined organic extracts were filtered through a pad of Celite. The filtrate was dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 5-(2-dimethylamino-ethyl)-3-methyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-one (242 mg, 97%) as a brown oil which was used as such.
Workup
- temperatureheated
- temperatureto reflux for another 4 hours
- temperatureThe reaction mixture was cooled down to 0° C. in an ice-water bath
- extractionextracted with dichloromethane (25 ml×5)
- filtrationThe combined organic extracts were filtered through a pad of Celite
- dry with materialThe filtrate was dried with anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-210fc5103095427e87d05121d32390c3
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08012966B2
Reaction notes
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