Hydrochloric Acid → 2-[2-(2-diethylaminoethylamino)ethyl]-4-methyl-1H-pyrrole-3-carboxylicacid ethyl ester

HRID 905709Notes

Reaction equation

HRID 905709 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10]([CH3:11])=[CH:9][NH:8][C:7]=1[CH2:12][C:13](=O)[NH:14][CH2:15][CH2:16][N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])=[O:5])[CH3:2].O.Cl.[OH-].[Na+]>O1CCCC1>[CH2:1]([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:5])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 666078542-[(2-diethylaminoethylcarbamoyl)methyl]-4-methyl-1H-pyrrole-3-carboxylic acid ethyl ester

Product 1

HCID 498404682-[2-(2-diethylaminoethylamino)ethyl]-4-methyl-1H-pyrrole-3-carboxylicacid ethyl esterYield 101.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A stirred solution of 2-[(2-diethylamino-ethylcarbamoyl)-methyl]-4-methyl-1H-pyrrole-3-carboxylic acid ethyl ester (310 mg, 1 mmol) in anhydrous tetrahydrofuran (2 ml) was added dropwise slowly with 1M borane-tetrahydrofuran complex in tetrahydrofuran (3 ml, 3 mmol) under an argon atmosphere. Upon completion of the addition, the mixture was stirred at room temperature for 1 hour and heated to reflux for another 5 hours. The reaction mixture was added with cold water (5 ml) and 1N hydrochloric acid (2 ml) dropwise, the mixture was stirred for 5 minutes, adjusted to pH 10 with 10% aqueous sodium hydroxide solution and extracted with ethyl acetate (10 ml×5). The combined organic extracts were washed with brine (15 ml), dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 2-[2-(2-diethylamino-ethylamino)-ethyl]-4-methyl-1H-pyrrole-3-carboxylic acid ethyl ester (300 mg) as a brown oil which was used as such.

Workup

  1. additionUpon completion of the addition
  2. temperatureheated
  3. temperatureto reflux for another 5 hours
  4. stirringthe mixture was stirred for 5 minutes
  5. extractionextracted with ethyl acetate (10 ml×5)
  6. washThe combined organic extracts were washed with brine (15 ml)
  7. dry with materialdried with anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a4135769f69442e789030f45a5647625
Source dataset
uspto-grants-2011_09
Patent number
US08012966B2

Reaction notes

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