Spiro[1,5-benzoxazepine-2(3H),4'-piperidine], 4,5-dihydro-1'-(phenylMethyl)- synthesis
- Product Name:Spiro[1,5-benzoxazepine-2(3H),4'-piperidine], 4,5-dihydro-1'-(phenylMethyl)-
- CAS Number:693789-32-1
- Molecular formula:C20H24N2O
- Molecular Weight:308.42
![SPIRO[2H-1-BENZOPYRAN-2,4'-PIPERIDIN]-4(3H)-ONE, 1'-(PHENYLMETHYL)-, OXIME](/CAS/20180703/GIF/693789-31-0.gif)
693789-31-0
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693789-32-1
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Yield:693789-32-1 81%
Reaction Conditions:
Stage #1: 1'-benzylspiro[chromene-2,4'-piperidin]-4(3H)-one oximewith diisobutylaluminium hydride in dichloromethane at 0; for 4 h;Beckmann rearrangement;
Stage #2: with sulfuric acid in methanol;dichloromethane;water at 0; for 0.333333 h;Beckmann rearrangement;
Stage #3: with sodium hydroxide in methanol;dichloromethane;water at 0; pH=> 9;Beckmann rearrangement;
Steps:
1. 1'-Benzyl-4,5-dihydro-3H-spiro[1,5-benzoxazepine-2,4'-piperidine] (13) [1-3]
General procedure: To a suspension of the oxime (1.00 g, 3.10 mmol) in CH2Cl2 (18 mL) was added DIBAL (1.0 mol/L in toluene, 18 mL) at 0 °C. The reaction mixture was stirred for 4 h at 0 °C and quenched by successive addition of MeOH (3 mL), H2O (3 mL), and aqueous H2SO4 (2 M, 17 mL). The resulting mixture was stirred at 0 °C for 20 min, basified (PH >9) with 10 N NaOH (8 mL), and extracted with EtOAc. The organic layer was dried (Na2SO4) and concentrated. Chromatography of the residue on SiO2 (KP-NH, 40-75 m, 100A, Biotage, CH2Cl2/EtOAc 10:1 to 1:1) gave 774 mg (81%) of 13 as a pale yellow oil. 1H NMR(400 MHz, CDCl3):δ 7.35-7.16 (5H, m), 6.96 (1H, dd, J = 7.9 and 1.5 Hz), 6.86 (1H, dt, J = 10.5 and 3.9 Hz), 6.73(1H, dt, J = 10.7 and 3.8 Hz), 6.62 (1H, dd, J = 7.8 and 1.6 Hz), 3.68 (1H, brs), 3.55 (2H, s), 3.28 (2H, t, J = 5.4 Hz), 2.62-2.59 (2H, m), 2.49 (2H, dt, J = 16.0 and 5.8 Hz), 1.98 (2H, d, J = 12.2 Hz), 1.92 (2H, t, J = 5.4 Hz), 1.66-1.59 (4H, m).
References:
Uto, Yoshikazu;Ueno, Yuko;Kiyotsuka, Yohei;Miyazawa, Yuriko;Kurata, Hitoshi;Ogata, Tsuneaki;Takagi, Toshiyuki;Wakimoto, Satoko;Ohsumi, Jun [European Journal of Medicinal Chemistry,2011,vol. 46,# 5,p. 1892 - 1896] Location in patent:supporting information; experimental part
![Spiro[1,5-benzoxazepine-2(3H),4'-piperidin]-4(5H)-one, 1'-(phenylMethyl)-](/CAS/GIF/1262757-32-3.gif)
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3612-20-2
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