Aluminium lithium hydride → Methyl(2-(morpholin-4-yl)ethyl)amine

HRID 2409806Notes

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].[O:7]1[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][NH:15][C:16](=O)OC(C)(C)C)[CH2:9][CH2:8]1>O1CCCC1>[CH3:16][NH:15][CH2:14][CH2:13][N:10]1[CH2:11][CH2:12][O:7][CH2:8][CH2:9]1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of LiAlH4 (7.72 g, 208.65 mmol, 3.00 equiv) in tetrahydrofuran (60 mL) at 0-5° C. was added dropwise a solution of tert-butyl 2-morpholinoethylcarbamate (16 g, 62.61 mmol, 1.00 equiv, 90%) in tetrahydrofuran (40 mL). The resulting solution was then stirred for 2 h at 70° C. in an oil bath. The reaction was then quenched by the addition of 7.7 mL of water, 7.7 mL of 15% sodium hydroxide, and 23.1 mL of water. The solids were filtered out. The mixture was dried over sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column and eluted with dichloromethane:methanol (0.5% triethylamine) (20:1) to afford 4.2 g (42%) of N-methyl-2-morpholinoethanamine as a brown oil.

Workup

customThe reaction was then quenched by the addition of 7.7 mL of water, 7.7 mL of 15% sodium hydroxide, and 23.1 mL of water
filtrationThe solids were filtered out
dry with materialThe mixture was dried over sodium sulfate
concentrationconcentrated under vacuum
washeluted with dichloromethane

Sources & evidence

ORD record: ord-17423fb730fd45ae98f29fcf3b672bfa
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815910B2

Reaction notes

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