Matarasso-Tchiroukhine, E. et al. published their research in Compt. rend. in 1959 | CAS: 3616-59-9

4-(2,2-Diethoxyethyl)morpholine (cas: 3616-59-9) belongs to ethers. Of all the functional groups, ethers are the least reactive ones. Ether bonds are quite stable towards bases, oxidizing agents and reducing agents. But on the other hand, ethers undergo cleavage by reaction with acids. Electron-deficient reagents are also stabilized by ethers. For example, borane (BH3) is a useful reagent for making alcohols. Pure borane exists as its dimer, diborane (B2H6), a toxic gas that is inconvenient and hazardous to use. Borane forms stable complexes with ethers, however, and it is often supplied and used as its liquid complex with tetrahydrofuran (THF).Safety of 4-(2,2-Diethoxyethyl)morpholine

Nitrogen derivatives of 2,3,6,7-tetramethoxy-9-methylfluorene was written by Matarasso-Tchiroukhine, E.. And the article was included in Compt. rend. in 1959.Safety of 4-(2,2-Diethoxyethyl)morpholine This article mentions the following:

Heterocyclic bases, morpholine and piperidine, in excess (25 mL.), refluxed (1 h.) with 2,3,6,7-tetramethoxy-9-(bromomethyl)fluorene (I) yield, resp., 2,3,6,7-tetramethoxy-9-(morpholinomethyl)fluorene (II) and 2,3,6,7-tetramethoxy – 9 – (piperidinomethyl)fluorene (III); this reaction is shown to proceed in 2 steps: (1) the base dehydrobrominates I to 2,3,6,7-tetramethoxy-9-[methylene]fluorene (IV), (2) the amine in excess adds on the methylenic double bond of IV, as confirmed, by the action of morpholine and piperidine with IV to give II and III. To prove their structure II and III are also synthesized by condensing, resp., di-Et ω-morpholinoacetal (V) and di-Et ω-piperidinoacetal (VI) with 3,4,3′,4′-tetramethoxybiphenyl, in the cold, in AcOH-H2SO4. V and VI are prepared from morpholine and piperidine with BrCH2CH(OEt)2. The compounds obtained, their characteristics and yields are: II, silky white needles (C6H6), m. 214-15°, picrate, orange-red needles (EtOH), m. 232° (decomposition), III, prismatic needles (MeOH), m. 169°, 60-80%; picrate, prismatic red needles (MeOH), crystallizes with 2 mols. MeOH, m. 155°; V, b16 123-4°, nD20 1.444, 73%; picrate, yellow needles (MeOH), m. 130-1°. VI, light yellow liquid, b16 102-4°, 50%; picrate, yellow prisms (aqueous MeOH), m. 68-9°. II and III refluxed with MeI in absolute EtOH (a large excess (20 mL.) of MeI and 17 h. refluxing are necessary in the case of III, 2 g.) give the corresponding quaternary ammonium salts, white crystals (EtOH), C23H30O5NI (VII), m. 245°; C24H32O4NI (VIII), decompose in the heat to IV, m. 237-8°; VII and VIII with picric acid in EtOH yield red picrates, crystallizing with 1 mL. H2O, m. with decomposition and m. 207°, resp. In the experiment, the researchers used many compounds, for example, 4-(2,2-Diethoxyethyl)morpholine (cas: 3616-59-9Safety of 4-(2,2-Diethoxyethyl)morpholine).

4-(2,2-Diethoxyethyl)morpholine (cas: 3616-59-9) belongs to ethers. Of all the functional groups, ethers are the least reactive ones. Ether bonds are quite stable towards bases, oxidizing agents and reducing agents. But on the other hand, ethers undergo cleavage by reaction with acids. Electron-deficient reagents are also stabilized by ethers. For example, borane (BH3) is a useful reagent for making alcohols. Pure borane exists as its dimer, diborane (B2H6), a toxic gas that is inconvenient and hazardous to use. Borane forms stable complexes with ethers, however, and it is often supplied and used as its liquid complex with tetrahydrofuran (THF).Safety of 4-(2,2-Diethoxyethyl)morpholine

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem