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| | 4-morpholinocyclohexanone Basic information |
| Product Name: | 4-morpholinocyclohexanone | | Synonyms: | 4-morpholinocyclohexanone;4-(Morpholin-4-yl)cyclohexan-1-one;4-(Morpholin-4-yl)cyclohexanone;4-Morpholinocyclohexan-1-one;4-(4-Morpholinyl)-cyclohexanone;Cyclohexanone, 4-(4-morpholinyl)- | | CAS: | 139025-93-7 | | MF: | C10H17NO2 | | MW: | 183.25 | | EINECS: | | | Product Categories: | | | Mol File: | 139025-93-7.mol |  |
| | 4-morpholinocyclohexanone Chemical Properties |
| storage temp. | 2-8°C | | solubility | Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly) | | form | Oil | | color | Dark Yellow to Dark Brown |
| | 4-morpholinocyclohexanone Usage And Synthesis |
| Uses | 4-(Morpholin-4-yl)cyclohexanone is a useful synthetic intermediate. It was used to synthesize diastereomeric 3,6-diaminobicyclo[3.1.0]hexane derivatives. | | Synthesis | The general procedure for the synthesis of 4-morpholin-4-ylcyclohexanone (VII-a) from the compound (CAS:127562-53-2) was as follows: to a solution of compound (4.50 g, 19.8 mmol) in tetrahydrofuran (THF, 100 mL) was added an aqueous 7N hydrochloric acid solution (40 mL). The reaction mixture was stirred at room temperature for 17 hours. Upon completion of the reaction, the mixture was poured into saturated aqueous sodium bicarbonate (NaHCO3) solution (475 mL) to quench the reaction. Subsequently, the reaction mixture was sequentially extracted with ethyl acetate (1 time) and dichloromethane (CH2Cl2, 3 times). The organic phases were combined, dried over anhydrous magnesium sulfate (MgSO4) and concentrated under reduced pressure. The resulting oil was purified by Kugelrohr distillation to afford the target product 4-morpholin-4-ylcyclohexanone (VII-a) (3.17 g, 87% yield) as a clear oil. The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3), δ 1.80-1.94 (m, 2H), 1.80-2.10 (m, 2H), 2.30 (m, 1H), 2.45-2.65 (m, 8H), and 3.74 (t, J=4.7 Hz, 4H). | | References | [1] Patent: WO2008/95943, 2008, A1. Location in patent: Page/Page column 175-176
[2] Patent: WO2008/95944, 2008, A1. Location in patent: Page/Page column 236; 238
[3] Patent: WO2010/15803, 2010, A1. Location in patent: Page/Page column 34-35
[4] Patent: WO2018/137593, 2018, A1. Location in patent: Page/Page column 105
[5] Synthesis, 1991, # 12, p. 1142 - 1147 |
| | 4-morpholinocyclohexanone Preparation Products And Raw materials |
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