|
|
| | 1-Phenyl-cyclopropylamine hydrochloride Basic information |
| Product Name: | 1-Phenyl-cyclopropylamine hydrochloride | | Synonyms: | TIMTEC-BB SBB008643;1-Phenylcyclopropanamine Hydrochloride;Cyclopropanamine, 1-phenyl-, hydrochloride (1:1);1-Phenylcyclopropan-1-amine hydrochloride;1-Phenyl-cyclopropylamine hydroc;1-PhenylcyclopropylaMine HCl;1-PhenylcyclopropanaMine, HCl;1-Amino-1-phenylcyclopropane hydrochloride, (1-Aminocycloprop-1-yl)benzene hydrochloride | | CAS: | 73930-39-9 | | MF: | C9H12ClN | | MW: | 169.65128 | | EINECS: | | | Product Categories: | API intermediates;Amines and Anilines | | Mol File: | 73930-39-9.mol |  |
| | 1-Phenyl-cyclopropylamine hydrochloride Chemical Properties |
| Melting point | 194.7-194.9 °C | | storage temp. | Inert atmosphere,Room Temperature | | form | solid | | Appearance | White to off-white Solid | | InChI | InChI=1S/C9H11N.ClH/c10-9(6-7-9)8-4-2-1-3-5-8;/h1-5H,6-7,10H2;1H | | InChIKey | ABUWJOHYZALSMF-UHFFFAOYSA-N | | SMILES | C1(N)(C2=CC=CC=C2)CC1.Cl |
| WGK Germany | WGK 3 | | HazardClass | IRRITANT | | HS Code | 2921490090 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Acute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | 1-Phenyl-cyclopropylamine hydrochloride Usage And Synthesis |
| Synthesis | The general procedure for the synthesis of 1-phenylcyclopropanamine hydrochloride from 1-phenyl-1-cyclopropanecarboxylic acid is as follows: first, 1-phenylcyclopropanecarboxylic acid (1) was reacted with sodium azide and sulfuric acid in chloroform to produce 1-phenylcyclopropanamine (2). Subsequently, 1-phenylcyclopropanamine was reacted with 2-methanesulfonyl chloride in chloroform under alkaline conditions to prepare to obtain the protected derivative (3), i.e., N-(1-phenylcyclopropyl) homotrimethylbenzenesulfonamide. Next, N-(1-phenylcyclopropyl)homotrimethylbenzenesulfonamide (3) was reacted with N-(4-bromobutyl)phthalimide (4) in DMF in the presence of sodium hydride overnight at room temperature to obtain N-(2- homotrimethylbenzenesulfonyl)-N-(1-phenylcyclopropyl)-4-phthalimidobutylamine (5). Then, phthaloyl was removed by reacting N-(2- homotrimethylbenzenesulfonyl)-N-(1-phenylcyclopropyl)-4-phthalimidobutylamine (5) with aniline hydrochloride and sodium methanol in methanol to produce N-(4-aminobutyl)-N-(1-phenylcyclopropyl)-2- homotrimethylbenzenesulfonamide (6). Next, the free amino group was again protected using 2- homotrimethylbenzenesulfonyl chloride in chloroform with hydrogen chloride to give N-(4-(homotrimethylbenzene-2-sulfonylamino)butyl)-N-(1-phenylcyclopropyl)-2- homotrimethylbenzenesulfonamide (7). Subsequently, a derivative of tetra- homotrimethylbenzene-2-sulfonyl-protected 1,2-bis((N-(1-phenylcyclopropyl)-4-aminobutyl)aminomethyl)cyclopropane (8) was prepared by reacting (7) with 1,2-bis(homotrimethylbenzene-2-sulfonyl- protected 1,2-bis((N-(1-phenylcyclopropyl)-4-amino-butyl)aminomethyl)cyclopropane) in DMF, in the presence of sodium hydride, at room temperature, overnight, to obtain (9). Finally, the homotrimethylbenzene-protecting group was removed using HBr in acetic acid and phenol in dichloromethane to give 1,2-bis((N-(1-phenylcyclopropyl)-4-aminobutyl)aminomethyl)cyclopropane (CGC-11255; SL-11255). | | References | [1] Patent: WO2006/86773, 2006, A2. Location in patent: Page/Page column 32-34
[2] Patent: WO2011/119704, 2011, A1. Location in patent: Page/Page column 35-36
[3] Synthetic Communications, 1980, vol. 10, # 2, p. 107 - 110 |
| | 1-Phenyl-cyclopropylamine hydrochloride Preparation Products And Raw materials |
|