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

HRID 247138Notes

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-596fb8a0cf224521a0e4d12b7b70f1b1
Source dataset: uspto-grants-1987_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04705840

Reaction notes

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