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Nitrile to Amine

(H₂ + Raney Ni)

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Examples:

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Example 1

To a solution of the SM (6.0 g, 22.0 mmol) in MeOH (60 mL) was added Raney Ni (6.0 g). The reaction was stirred under H2 at 70 psi for 16 h, after which time the mixture was filtered through celite. The filtrate was concentrated in vacuo and the resulting material was purified by a neutral alumina column to provide the product as a thick brown liquid. [4.2 g, 69%]

[Patent Reference: WO2014149164, page 214, (23.7 MB)]

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Example 2

To a solution of the SM (60 mg, 0.19 mmol) in MeOH (5 mL) was added Raney Ni (6 mg, 10% w/w). The reaction mixture was stirred at RT under H2 for 2 h. After filtration, the filtrate was concentrated and purified by Prep HPLC [5-95% (MeOH)/(H2O with 0.05% NH4OH)] to provide the product as a yellow solid. [32 mg, 53%]

[Patent Reference: WO2016011390, page 60, (20.2 MB)]

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Example 3

A mixture of the SM (180 g, 1.10 mol), Raney Ni (40.0 g), and NH4OH (250 mL) in MeOH (1.0 L) was stirred under H2 (50 psi) at RT for 5 h. The mixture was filtered and concentrated to provide the product which was taken on without further purification. [165.0 g]

[Patent Reference: WO2016014463, page 91, (6.7 MB)]