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ChemicalBook CAS DataBase List 1-N-Boc-4-(Phenylamino)piperidine

1-N-Boc-4-(Phenylamino)piperidine synthesis

10synthesis methods
79099-07-3 Synthesis
N-(tert-Butoxycarbonyl)-4-piperidone

79099-07-3
549 suppliers
$5.00/5g

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Yield:125541-22-2 98%

Reaction Conditions:

with sodium hydroxide;sodium tris(acetoxy)borohydride;glacial acetic acid;aniline in diethyl ether;dichloromethane;

Steps:

4-Phenylamino-piperidine-1-carboxylic Acid Tert.-butyl Ester

Reaction Scheme 1, Step 1 4-Phenylamino-piperidine-1-carboxylic Acid Tert.-butyl Ester A solution of N-tert-butoxycarbonyl-4-piperidone (Lancaster 13361, 7 g) and aniline (Aldrich 24228-4, 3.3 g) in dichloromethane (200 ml) was treated with sodium triacetoxyborohydride (Aldrich 31639, 10.4 g) followed by acetic acid (2.1 g) and the mixture stirred for 2 h at ambient temperature. 1M Aqueous sodium hydroxide solution (100 ml) was added, followed by diethyl ether (200 ml) and the mixture stirred vigorously for 5 min. The organic phase was separated, washed with water (100 ml), followed by brine (100 ml), dried (anhydrous magnesium sulphate), filtered and evaporated to give the title compound as a white solid (9.5 g, 98%). Mass spectrum 277 [M+H]+.

References:

US2003/69276,2003,A1

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