Ethylene Oxide → HCID 20446373, compound

HRID 2418460Notes

Reaction equation

[CH2:1]1[O:3][CH2:2]1.[CH3:4][C:5]1([CH3:21])[CH2:10][CH:9]([N:11]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:12]2=[O:18])[CH2:8][C:7]([CH3:20])([CH3:19])[NH:6]1>CN(C)C=O>[OH:3][CH2:2][CH2:1][N:6]1[C:7]([CH3:20])([CH3:19])[CH2:8][CH:9]([N:11]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:12]2=[O:18])[CH2:10][C:5]1([CH3:21])[CH3:4]

Participants

Conditions

Temperature: 190 °C

Procedure

To a small autoclave is charged a solution of 6.6 g (0.15 mole) of ethylene oxide and 25.2 g (0.1 mole) of N-(2,2,6,6-tetramethylpiperidin-4-yl)-epsilon-caprolactam, in 100 ml of N,N-dimethylformamide. The autoclave is heated for four hours at 190° C. during which time the pressure dropped from 100 psi (7 kg/cm2) to 70 psi (4.9 kg/cm2). The reaction mixture is then distilled in vacuo (50° C./2 mm) to remove the solvent. The residue is crystallized from 300 ml of heptane:toluene (2:1) to give the above-named product in a yield of 13.7 g as a white solid melting at 141°-142° C.

Workup

additiondropped from 100 psi (7 kg/cm2) to 70 psi (4.9 kg/cm2)
distillationThe reaction mixture is then distilled in vacuo (50° C./2 mm)
customto remove the solvent
customThe residue is crystallized from 300 ml of heptane:toluene (2:1)

Sources & evidence

ORD record: ord-a0272b069b9445428c364db09ad0e732
Source dataset: uspto-grants-1984_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04472547

Reaction notes

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