Configuration of nitrogen-containing compounds. VI. Configuration of substituted 2-aminocyclohexanols was written by Kovar, Jan;Blaha, Karel. And the article was included in Chemicke Listy pro Vedu a Prumysl in 1958.Synthetic Route of C13H19NO This article mentions the following:
The rate of solvolysis of N-R-substituted-2-(p-nitrophenyl)-4,5-tetra-methylenoxazolidine (I) obtained by condensing N-R-substituted-2-aminocyclohexanols (II) with p-O2NC6H4CHO was studied in regard to the steric structure of the starting amino alcs. trans-II (R = Me) obtained in 8.5 g. yield by shaking 24 hrs. a mixture of 13.4 g. trans-2-chlorocyclohexanol and 15 ml. solution containing 0.15 mole NH2Me, adding 50 ml. N HCl, extracting undissolved oil with Et2O, alkalizing the aqueous solution with NaOH, extracting with 4:1 CHCl3-Et2O, and evaporating the solvent gave an oily residue, b21 113掳, which crystallized, m. 22-4掳; HCl salt, m. 121掳 (9:1 Me2CO-MeOH). Heating a solution of 4 g. trans-II (R = H) and 3.2 g. PhCH2NH2 in 7 ml. EtOH 8 hrs. to 145-55掳 in a sealed tube, dissolving the crystalline product in 50 ml. H2O, and working up as above gave 2.0 g. trans-II (R = PhCH2) b0.6 125-7掳, m. 73掳 (petr. ether); picrate, m. 134-5掳 (50% EtOH); HCl salt, m. 204-5掳 (Me2CO-EtOH 9:1); trans-N-benzoyl derivative (III) obtained in 77% yield by the usual method gave crystals, m. 116.5-17.5掳 (C6H6-petr. ether). Hydrogenating 27 g. 慰-AcNHC6H4OH over Raney Co in EtOH at 150-60掳 and 100 atm. 12 hrs., filtering off the catalyst, evaporating the solvent in vacuo, and treating the residue with 10 ml. Me2CO gave 5.8 g. crystals of cis-II (R = Ac) (IV), m. 143-4掳. IV (4.7 g.) boiled 2 hrs. with 2.33N HCl and worked up as usual gave 4.3 g. HCl salt of cis-II (R = H), m. 186-6.5掳; free base, m. 73-5掳. cis-II (R = Me) was obtained according to Mousseron, et al. (C.A. 47, 9319a), m. 38-40掳; HCl salt, m. 205-6掳 (1:1 EtOH-Me2CO); picrate, m. 141-2掳 (H2O). cis-II (R = PhCH2) was obtained by heating a solution of III in SOCl2 2.5 hrs. to 60掳, pouring the product into Et2O, and refluxing the undissolved portion 5 hrs. with 10% HCl, or by distilling a solution of 747 mg. cis-II (R = H) and 1.5 g. PhCHO in 25 ml. C6H6 with simultaneous dropwise addition of C6H6, dissolving the residue in Et2O, and boiling 6 hrs. with 1 g. LiAlH4 to give crystalline HCl salt, m. 248-50掳 (1:1 EtOH-Me2CO); free base, m. 67掳 (petr. ether); picrate, m. 157-8掳 (H2O). The following I were obtained by heating slowly to boiling equivalent amounts of II and p-O2NC6H4CHO in PhCl (50 ml. per 10 millimoles with continuous removal of H2O. The products were crystallized from petr. ether or petr. ether-C6H6: cis-I (R = H), m. 73-3.5掳 (yield 93%); cis-I (R = Me), m. 68-9掳 (82%); cis-I (R = PhCH2), m. 59-61掳 (94%); trans-I (R = H), m. 127掳 (65%); trans-I (R = Me), m. 77-8掳 (78%); trans-I (R = PhCH2), m. 97.5-99掳 (50%). Treatment of I with 2,4-(O2N)2C6H3NHNH 2 in EtOH at 24掳 catalyzed with H2SO4 brought about opening of the ring. Its rate was followed by determining gravimetrically the separated 4-O2NC6H4CH:NNHC6H3(NO2)2-2,4. The reaction constants of the cis and trans isomers are, resp.: I (R = H) 9.81 脳 10-3, 4.7 脳 10-2; I (R = Me) 8.12 脳 10-4, 8.0 脳 10-2; I (R = PhCH2) 1.31 脳 10-3, 1 脳 10-1. In the experiment, the researchers used many compounds, for example, Trans-2-(benzylamino)cyclohexanol (cas: 40571-86-6Synthetic Route of C13H19NO).
Trans-2-(benzylamino)cyclohexanol (cas: 40571-86-6) belongs to alcohols. Because alcohols are easily synthesized and easily transformed into other compounds, they serve as important intermediates in organic synthesis. A multistep synthesis may use Grignard-like reactions to form an alcohol with the desired carbon structure, followed by reactions to convert the hydroxyl group of the alcohol to the desired functionality.Synthetic Route of C13H19NO
Referemce:
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Alcohols – Chemistry LibreTexts