Propylene Oxide → 4-Morpholineethanol, .alpha.-methyl-

HRID 2351019Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH2:7]1[O:10][CH:8]1[CH3:9]>>[OH:10][CH:8]([CH3:9])[CH2:7][N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

Reactant 2

HCID 6378Propylene Oxide

HCID 8083Morpholine

Product 1

HCID 979574-Morpholineethanol, .alpha.-methyl-Yield 96.1%

Procedure

An amount, 871.2 grams, of morpholine (10 moles) and 580.8 grams of propylene oxide (10 moles) were mixed in a 2 liter flask and set aside for seven days at room temperature. At the end of this time, the solution was distilled under vacuum to give 1396.0 grams (96.1%) of N-(2-hydroxypropyl)-morpholine as a colorless oil, bp 63°-65° C. at 0.25 mm of Hg. Gas chromatographic analysis of the product showed the presence of only one compound which indicated no position isomer was formed. The identity of the product was confirmed by elemental analysis, calc. 57.9 C, 10.4 H, 9.65 N; found 57.5 C, 10.3 H, 9.5 N.

Workup

distillationAt the end of this time, the solution was distilled under vacuum

Sources & evidence

ORD record: ord-be2c69d5bfdb4913b21d7e4bf82bac78
Source dataset: uspto-grants-1989_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04871845

Reaction notes

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