1-BOC-4-(4-BROMO-PHENYLAMINO)-PIPERIDINE synthesis

Yield:443998-65-0 72%

Reaction Conditions:

Stage #1:N-tert-butyloxycarbonylpiperidin-4-one;4-bromo-aniline with sodium tris(acetoxy)borohydride;acetic acid in dichloromethane at 25; for 17 h;
Stage #2: with sodium hydroxide in dichloromethane;water

Steps:

2.1
EXAMPLE 2 [0170] [CHEMMOL-00477] [0171] Step 1 [0172] 4-Bromo aniline (8.3 g, 48 mmol), N-Boc-4-piperidone (8.0 g, 40 mmol), Na(AcO)3BH (12.7 g, 60 mmol), and AcOH (3.5 mL, 60 mmol) were taken up in CH2Cl2 and stirred at 25° C. (17 h). The solution was diluted with CH2Cl2 and quenched with 1 N NaOH. The aqueous layer was extracted with CH2Cl2. The combined organic layers were dried (Na2SO4), filtered and concentrated. Purification via recrystallization (CH2Cl2/hexanes) gave 10.2 g (72%) of an amine product.

References:

Schering Corporation US2004/10008, 2004, A1 Location in patent:Page/Page column 28-29; 35

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