Aluminium lithium hydride → 4-[3-(4-Bromophenyl)propyl]morpholine

HRID 931514Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[Br:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=O)=[CH:10][CH:9]=1>O1CCCC1>[Br:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][N:18]2[CH2:19][CH2:20][O:21][CH2:22][CH2:23]2)=[CH:10][CH:9]=1

Participants

Conditions

Temperature: -30 °C

Procedure

To a mixture of lithium aluminum hydride (4.4 g, 115.79 mmol, 2.00 equiv) in tetrahydrofuran (120 mL) maintained under nitrogen at −30° C. was added a solution of 3-(4-bromophenyl)-1-morpholinopropan-1-one (17.2 g, 57.91 mmol, 1.00 equiv) in tetrahydrofuran (80 mL) dropwise with stirring. The resulting solution was stirred at −30° C. for 30 min and at room temperature for 2 h. The reaction was quenched by the sequential addition of 4.4 mL of water, 13 mL of 15% aqueous sodium hydroxide solution and 4.4 mL of water. The solid was removed by filtration and the filtrate was extracted with 1×350 mL of ethyl acetate. The organic layer was washed with 2×50 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum to afford 13.5 g (82%) of 4-(3-(4-bromophenyl)propyl)morpholine as a light yellow oil.

Workup

stirringThe resulting solution was stirred at −30° C. for 30 min and at room temperature for 2 h
customThe reaction was quenched by the sequential addition of 4.4 mL of water, 13 mL of 15% aqueous sodium hydroxide solution and 4.4 mL of water
customThe solid was removed by filtration
extractionthe filtrate was extracted with 1×350 mL of ethyl acetate
washThe organic layer was washed with 2×50 mL of brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-5d65964132ca478395b2a84eec84562f
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296732B2

Reaction notes

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