|
【结 构 式】 
|
【分子编号】44237 【品名】2-(dimethylamino)-1-ethanol 【CA登记号】108-01-0 |
【 分 子 式 】C4H11NO 【 分 子 量 】89.13748 【元素组成】C 53.9% H 12.44% N 15.71% O 17.95% |
合成路线1
该中间体在本合成路线中的序号：(VI)Lithiation of N-methylpyrazole (I) by means of n-butyllithium, followed by addition to 2-thiophenecarboxaldehyde (II), afforded carbinol (III). This compound was alternatively obtained by sodium borohydride reduction of diheteroaryl ketone (IV). Condensation of alcohol (III) with either 2-(dimethylamino)ethyl chloride (IV) in the presence of NaOH or 2-(dimethylamino)ethanol (VI) under catalysis of H2SO4 furnished ether (VII). This compound was finally converted to the title citrate salt by treatment with citric acid in EtOH.
| 【1】 Frigola-Constansa, J.; Andaluz-Mataro, B.; Merce-Vidal, R. (Laboratorios del Dr. Esteve, SA); Thienylazolylalcoxyethanamines, their preparation and their application as medicaments. WO 9952525 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 44234 | 1-methyl-1H-pyrazole; N-Methylpyrazole | 930-36-9 | C4H6N2 | 详情 | 详情 |
| (II) | 30732 | 2-thiophenecarbaldehyde; Thiophene-2-carboxaldehyde | 98-03-3 | C5H4OS | 详情 | 详情 |
| (III) | 44235 | (1-methyl-1H-pyrazol-5-yl)(2-thienyl)methanol | C9H10N2OS | 详情 | 详情 | |
| (IV) | 44236 | (1-methyl-1H-pyrazol-5-yl)(2-thienyl)methanone | C9H8N2OS | 详情 | 详情 | |
| (V) | 11907 | Dimethylaminoethyl chloride; 2-Dimethylaminoethyl chloride; 2-Chloro-N,N-dimethyl-1-ethanamine; N-(2-Chloroethyl)-N,N-dimethylamine | 107-99-3 | C4H10ClN | 详情 | 详情 |
| (VI) | 44237 | 2-(dimethylamino)-1-ethanol | 108-01-0 | C4H11NO | 详情 | 详情 |
| (VII) | 44238 | N,N-dimethyl-2-[(1-methyl-1H-pyrazol-5-yl)(2-thienyl)methoxy]-1-ethanamine; N,N-dimethyl-N-[2-[(1-methyl-1H-pyrazol-5-yl)(2-thienyl)methoxy]ethyl]amine | C13H19N3OS | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(II)The reaction of dimethyl naphthalene-1,5-disulfonate (I) with dimethylaminoethanol (II) gives bis (2-hydroxyethyltrimethylammonium)naphthalene-1,5-disulfonate (III), which is then condensed with 2-acetoxypropionic anhydride (IV) in refluxing acetonitrile
| 【1】 Miura, K.; et al. (Tomaya Chem. Co., Ltd.); DE 2425983; FR 2233045; GB 1436978 FR 2233045; JP 7513320; JP 7518413; JP 7721490; JP 7785118; JP 7837334; JP 8001251; US 3903137 . |
| 【2】 Castaner, J.; Prous, J.; Aclatonium Napadisilate. Drugs Fut 1982, 7, 4, 227. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 60645 | dimethyl 1,5-naphthalenedisulfonate | C12H12O6S2 | 详情 | 详情 | |
| (II) | 44237 | 2-(dimethylamino)-1-ethanol | 108-01-0 | C4H11NO | 详情 | 详情 |
| (III) | 60646 | 2-{[2-(acetyloxy)propanoyl]oxy}-N,N,N-trimethyl-1-ethanaminium 2-hydroxy-N,N,N-trimethyl-1-ethanaminium 1,5-naphthalenedisulfonate | C25H40N2O11S2 | 详情 | 详情 | |
| (IV) | 60647 | 1-(acetyloxy)propanoic anhydride | C10H14O7 | 详情 | 详情 |
合成路线3
该中间体在本合成路线中的序号：(III)Treatment of 1,2-epoxyhexadecane (I) with concentrated HBr at 65 C gives rise to bromohydrin (II). This is then condensed with N,N-dimethyl ethanolamine (III) to produce the title ammonium salt.
| 【1】 Rutzen, H. (Henkel KgA); Process for preparing quaternary ammonium cpds.. DE 3136628; EP 0075066; JP 1983046043; US 4480126 . |
合成路线4
该中间体在本合成路线中的序号：(IV)In a related procedure, halogenation of 1-hexadecene (I) with N-bromosuccinimide in THF/H2O leads to a mixture of regioisomeric bromohydrins (II) and (III). Refluxing of this mixture of bromohydrins with N,N-dimethyl ethanolamine (IV) in MeOH gives rise to the title ammonium salt as the only isomer.
| 【1】 Wong, Y.-L.; et al.; Spermicidal, anti-HIV, and micellar properties of di- and trihydroxylated cationic surfactants. Tetrahedron 2002, 58, 1, 45. |