Ishidate, Morizo; Sakurai, Yoshio; Aiko, Isao published an article in 1960, the title of the article was Cancerocidal substances. XXVI. Preparation of bis(2-chloroethyl)amine derivatives and related N-oxides.COA of Formula: C8H19NO2 And the article contains the following content:
Fourteen new RN(CH2CH2Cl)2 (I) and 6 of their N-oxides were prepared and tested for their in vivo and in vitro antitumor activity against the Yoshida sarcoma. The methods used were previously described (CA 49, 8304h). The intermediate RN(CH2CH2OH)2 (II) were prepared by either method A, [RX + HN(CH2CH2OH)2], or method B, (RNH2 + 2CH2.CH2O) (R, method used, phys. constants of II or its derivatives given): tert-Bu, B, b8 132-5掳; C12H25, A or B, b4 200-10掳; 2-(10-phenothiazinyl)ethyl (III), A, b0.02 250-60掳; 9-camphoryl (IV), B, HCl salt m. 218-20掳 (decomposition), picrate m. 116-19掳; MeOCH2CH2, A, b4 133-40掳; BuOCH2CH2, A, b7 154-60掳; PhOCH2CH2, A, b4 200-10掳; (MeO)2CHCH2, A, b4 127-33掳, b5 165-9掳; (EtO)2CHCH2, A, b4 138-42掳, b4 161-5掳; and (BuO)2CHCH2, A, b4 175-6掳. II were chlorinated without further purification to give I, which were oxidized to the corresponding N-oxides in 6 cases (R, phys. constants of I or its derivatives given): tert-Bu (30% yield), HCl salt m. 178-9掳, N-oxide (48%) picrate m. 95-6掳, and HCl salt m. 89掳; C6H13, b7.5 125-9掳, HCl salt m. 78-82掳; C12H25, picrylsulfonate m. 92-3掳; III, HCl salt m. 96-8掳; IV, HCl salt m. 218-20掳 (decomposition), [伪]23D -60.6掳 (c 1.58, H2O), N-oxide HCl salt m. 178-80掳 (decomposition); MeOCH2CH2, HCl salt m. 130掳, N-oxide HCl salt m. 109-11掳 and picrate m. 89-90掳; BuOCH2CH2, HCl salt m. 126-7掳, N-oxide HCl salt m. 75-6掳, and picrate m. 81-2掳; PhOCH2CH2, HCl salt m. 150-1掳, picrate m. 117-18掳, N-oxide HCl salt m. 173-4掳 (decomposition) and picrate m. 126-7掳; (MeO)2CHCH2, HCl salt m. 129-30掳, N-oxide HCl salt m. 110掳 and picrate m. 89-90掳; (EtO)2CHCH2, HCl salt m. 132-3掳; and (BuO)2CHCH2, b3 111-13掳, HCl salt m. 121-2掳. The 3 remaining compounds of this series were: the N-oxide of I (R = EtOCH2CH2), which had been previously prepared (loc. cit.); I (R = OHCCH2) (picrate m. 131掳), prepared by hydrolysis of I [R = (MeO)2CHCH2] by heating it 5 hrs. at 80掳 with 20% HCl; and I (R = AcCH2CH2) (picrate m. 113-15掳), prepared by warming 1.5 hrs. at 40-5掳 41 g. HCl salt of I (R = H) with 23 cc. 30% HCHO, and 95 cc. Me2CO. The 9-aminocamphor (m. 172掳; HCl salt m. 334掳 (decomposition); toluenesulfonamide m. 182掳) for the preparation of II (R = IV) was prepared in 70 g. yield by the catalytic hydrogenation (Raney Ni) of a mixture of 71 g. 9-oxocamphor oxime and 100 g. liquid NH3 in 300 cc. EtOH. The results of tests of these 20 compounds for biol. activity and toxicity were reported and discussed. A few were very effective against Yoshida sarcoma. The experimental process involved the reaction of 2,2′-(tert-Butylazanediyl)diethanol(cas: 2160-93-2).COA of Formula: C8H19NO2
2,2′-(tert-Butylazanediyl)diethanol(cas:2160-93-2) belongs to alcohols. In general, the hydroxyl group makes alcohols polar. Those groups can form hydrogen bonds to one another and to most other compounds. Owing to the presence of the polar OH alcohols are more water-soluble than simple hydrocarbons. COA of Formula: C8H19NO2
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts