Ethanolamine → (E)-4-phenyl-2-butenyloxyamine

HRID 1899769Notes

Reaction equation

C(C[NH2:4])O.C1(=O)NC(=O)[C:7]2=[CH:11][CH:12]=[CH:13][CH:14]=[C:6]12.CC[O:18][CH2:19][CH3:20].C(O[CH2:25][CH3:26])(=O)C>>[C:6]1([CH2:25]/[CH:26]=[CH:20]/[CH2:19][O:18][NH2:4])[CH:7]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

Reactant 3

HCID 700Ethanolamine

HCID 8857Ethyl Acetate

HCID 18959638Ether phthalimide

Product 1

HCID 14647066(E)-4-phenyl-2-butenyloxyamine

Conditions

Temperature: 60 °C

Procedure

At 60° C. and while stirring, 11.6 g (0.19 mol of ethanolamine is added to 55.5 g (0.19 mol of the phthalimide ether c) in 190 ml of ethyl acetate. After 5 hours, the precipitated N-(hydroxyethyl)-phthalimide is filtered off and 18.8 g of oxalic acid in 30 ml of ethyl acetate is added to the filtrate. There is obtained 95% of theory of (E)-4-phenyl-2-butenyloxyamine as the oxalate salt. Melting point: 127°-129° C.

Workup

filtrationthe precipitated N-(hydroxyethyl)-phthalimide is filtered off
addition18.8 g of oxalic acid in 30 ml of ethyl acetate is added to the filtrate

Sources & evidence

ORD record: ord-cd60e042ac8a4dbeb30c2f96819a7767
Source dataset: uspto-grants-1996_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05574000

Reaction notes

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