Aluminium lithium hydride → 4-[3-(2,4-dimethyl-1H-pyrrol-3-yl)-propyl]-morpholine

HRID 1372385Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[NH:9][CH:10]=[C:11]([CH3:23])[C:12]=1[CH2:13][CH2:14][C:15]([N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)=O>O1CCCC1.[OH-].[Na+]>[CH3:7][C:8]1[NH:9][CH:10]=[C:11]([CH3:23])[C:12]=1[CH2:13][CH2:14][CH2:15][N:17]1[CH2:18][CH2:19][O:20][CH2:21][CH2:22]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a suspension of 2.67 g (70 mmol) of lithium aluminum hydride in 100 mL of tetrahydrofuran was added dropwise a solution of 13.84 g (59 mmol) of 3-(2,4-dimethyl-1H-pyrrol-3-yl)-1-morpholin-4-yl-propan-1-one in 50 mL of tetrahydrofuran. The reaction mixture was stirred at 80° C. for 1 hour and cooled in an ice bath. Ice cubes were slowly added to the mixture until no more gas was generated. A few drops of 2 N sodium hydroxide were added and the reaction mixture was stirred at room temperature for 30 min, extracted with ethyl acetate and the extract dried over anhydrous sodium sulfate and concentrated to give 10.37 g (79% yield) of 4-[3-(2,4-dimethyl-1H-pyrrol-3-yl)-propyl]-morpholine as a light brown oil which was used without further purification.

Workup

temperaturecooled in an ice bath
additionIce cubes were slowly added to the mixture until no more gas
stirringthe reaction mixture was stirred at room temperature for 30 min
extractionextracted with ethyl acetate
dry with materialthe extract dried over anhydrous sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-151e319a9177450cabcfdc1d70a319a0
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07157577B2

Reaction notes

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