Hydrochloric Acid → 5-(2-Diethylamino-ethyl)-3-methyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-4-one

HRID 905710Notes

Reaction equation

HRID 905710 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]([CH2:20][CH3:21])[CH2:18][CH3:19])=O)C.C[Al](C)C.Cl.[OH-].[Na+]>C1(C)C=CC=CC=1.O>[CH2:18]([N:17]([CH2:20][CH3:21])[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])[CH3:19]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 16682925TrimethylaluminumHCID 498404682-[2-(2-diethylaminoethylamino)ethyl]-4-methyl-1H-pyrrole-3-carboxylicacid ethyl ester

Product 1

HCID 250230145-(2-Diethylamino-ethyl)-3-methyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-4-oneYield 97.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

A stirred solution of 2-[2-(2-diethylamino-ethylamino)-ethyl]-4-methyl-1H-pyrrole-3-carboxylic acid ethyl ester (295 mg, 1 mmol) in 5 ml of toluene was added dropwise slowly with 2 M 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., added with 1N hydrochloric acid (3 ml) and cold water (10 ml), and stirred for 5 minutes. The mixture was adjusted to pH 12 with 10% aqueous sodium hydroxide solution and extracted with dichloromethane (30 ml×4). 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-diethylamino-ethyl)-3-methyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-4-one (242 mg, 97%) as a brown oil.

Workup

  1. temperatureheated
  2. temperatureto reflux for another 4 hours
  3. temperatureThe reaction mixture was cooled down to 0° C.
  4. stirringstirred for 5 minutes
  5. extractionextracted with dichloromethane (30 ml×4)
  6. filtrationThe combined organic extracts were filtered through a pad of Celite
  7. dry with materialThe filtrate was dried with anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-12d7d3598bd4471daeea281e3ba484d7
Source dataset
uspto-grants-2011_09
Patent number
US08012966B2

Reaction notes

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