Ethyl formate → N-[2-(morpholin-4-yl)ethyl]formamide

Reaction equation

[NH2:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1.[CH:10](OCC)=[O:11]>>[CH:10]([NH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1)=[O:11]

Participants

Reactant 2

HCID 8025Ethyl formate

HCID 4082852-Morpholinoethylamine

Product 1

HCID 12951904N-[2-(morpholin-4-yl)ethyl]formamideYield 100%

Procedure

The procedure of B. V. Cheney et al. [J. Med. Chem., 28, 1853-1864 (1985)) was used. A solution of 4-(2-aminoethyl)morpholine (1.00 g, 76.8 mmol) and ethyl formate (213 mL, 2640 mmol) was refluxed overnight under an atmosphere of nitrogen. Vacuum distillation gave 1.46 g (100% yield) of a clear, colorless liquid (bP0.3 18°-120° C.). The 1H NMR spectral data were consistent with the structure of the title compound.

Workup

distillationVacuum distillation
customgave 1.46 g (100% yield) of a clear, colorless liquid (bP0.3 18°-120° C.)

Sources & evidence

ORD record: ord-465544de9a6e46c0ad14764ed8196d18
Source dataset: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05411959

Reaction notes

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