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  (Process Chem)


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Substitution (Cl)

(Aliphatic Amines)


Example 1

A 4mL vial was charged with the alkyl chloride (A) (0.125 g, 0.60 mmol), the amine (B) (0.054 g, 0.30 mmol), NaI (0.149 g, 1.00 mmol), K2CO3 (0.138 g, 1.00 mmol), and DMF (1 mL). The reaction mixture was stirred at 95 C for 2 days. The mixture was diluted with H2O and extracted with EtOAc. The crude material was purified by cation-exchange column chromatography then silica gel column chromatography (EtOAc) to provide the product. [0.033 g]

[Patent Reference: WO2014152144, page 62, (4.6 MB)]

Example 2

To a mixture of the alkyl chloride (A) (0.85 g, 4.25 mmol) and morpholine (B) (0.44 mL, 5.1 mmol) in DMF (10 mL) was added DIEA (1.08 mL, 6.37 mmol) at RT. After stirring for 16 h, the excess solvent was removed in vacuo. The residue was diluted with ice-H2O and the solids were collected by filtration. The solids were triturated with ether to provide the product as a yellow solid. [0.8 g, 75%]

[Patent Reference: WO2015088045, page 127, (10.3 MB)]