1-BOC-4-(4-CHLORO-BENZOYL)-PIPERIDINE synthesis

10synthesis methods

Product Name:1-BOC-4-(4-CHLORO-BENZOYL)-PIPERIDINE
CAS Number:209808-06-0
Molecular formula:C17H22ClNO3
Molecular Weight:323.81

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139290-70-3 Synthesis

1-Boc-4-[methoxy(methyl)carbamoyl]piperidine

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Yield:209808-06-0 3340 mg

Reaction Conditions:

Stage #1: 1-Chloro-4-iodobenzenewith isopropylmagnesium chloride in tetrahydrofuran; for 2 h;
Stage #2: tert-butyl 4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate in tetrahydrofuran; for 3 h;

Steps:

20.1-a Step 1-a: Preparation of ferf -butyl 4-(4-chlorobenzoyl)piperidine-l-carboxylate:

To a stirred isopropylmagnesium chloride solution, 2N in THF (8.25 mL; 16.5 mmol) was added a solution of l-chloro-4-iodobenzene (3580 mg; 14.9 mmol) in THF (20 mL) over 5 min. After stirring for 2 h, a solution of tert-butyl 4-[methoxy(methyl)carbamoyl]piperidine-l-carboxylate (4540 mg; 16.3 mmol) in THF (15 mL) was added and the reaction mixture was further stirred for 3 h. Volatiles were removed under reduced pressure and the residue was dissolved in EA (100 mL). The solution was successively washed with a saturated aqueous solution of NH₄C1 (3 x 30 mL) and brine (2 x 30 mL), dried over Na₂S0₄, filtered and concentrated to dryness. The residue was purified by column (0865) chromatography (silica gel; PE : EA; 20: 1 to 10: 1 ; v/v) to afford tert-butyl 4-(4-chlorobenzoyl)piperidine- 1 -carboxylate (3340 mg) as a white solid. (0866) MS m/z (+ESI): 324.1, 326.1 [M+H]⁺. (0867) 'H-NMR (400 MHz, DMSO-i) δ ppm: 8.00 (d, J = 8.8 Hz, 2H), 7.60 (d, J = 8.8 Hz, 2H), 3.98 - 3.94 (m, 2H), 3.65 - 3.55 (m, 1H), 2.95 - 2.82 (m., 2H), 1.77 - 1.73 (m, 2H), 1.46-1.36 (m, 11H).

References:

WO2019/72978,2019,A1 Location in patent:Page/Page column 88

24424-99-5 Synthesis