Piperazine compounds. III. Syntheses of 1-piperazinylalkyltheophylline derivatives was written by Ikeda, Yoshiaki. And the article was included in Yakugaku Zasshi in 1969.Application of 21867-64-1 This article mentions the following:
The following I were prepared by known methods (R, X, % yield, and b.p./mm. or m.p. given): Pr, H, 42, 45.5-7°/10 (dipicrate, m. 234-6.5°); p-ClC6H4CH2, CH2CH(OH)CHCl, 83, 78-9°. Theophylline (II) (10.9 g.), 2.3 g. NaOH, and 42 ml. H2O treated at 80-5° with 12.5 ml. BrCH2CH2Br in 20 ml. iso-PrOH over 1 hr. and refluxed 7-8 hrs. gave 48% QCH2CH2Br (Q = 7-theophyllinyl in this abstract) (III), m. 144-5°. The following IV were prepared by heating III with 2 moles I (X = H) 7-8 hrs. in EtOH (R, % yield, and m.p. given): Et, 98, 93-4°; Pr, 70, – (2HCl salt m. 278-80°); allyl, 82, 87-8°; Bu, 95, 77-9°; HOCH2CH2, 68, – (2HCl.H2O salt m. 268-9°); HO(CH2)3, 47, 114-15°; Ph-CH2 (IVa), 95, 120-1°; p-ClC6H4CH2, 70, 152-2.5°; o-ClC6H4-CH2, 72, 159.5-60.5; m-ClC6H4CH2, 71, 127.5-9.5°; PhCH2CH2, 73, – (2HCl salt m. 264-6°); EtO2C, 84, 135.5-7.5°; Ac, 71, 140-1°; Bz, 90, 184-5°. Similarly prepared were V.2HCl (same data given): Pr, 96, 302-3°; allyl, 73, 269-70°; Bu, 61, – (base m. 70-1°); HOCH2CH2, 92, – (base m. 80-2°); HO(CH2)3, 82, 108-11°; PhCH2, 95, 285-6°. The following VI were prepared by heating 7-(2,3-epoxypropyl)theophylline with 1.2 moles I (X = H) in EtOH (besides a little QCH2CH(OH)CH2Q, m. 267-8°) (same data given): Et, 30, 145-5.5°; Pr, 65, 153-4°; allyl, 45, 140.5-1°; Bu, 74, 146-7°; HOCH2CH2, 82, 153.5-4.5°; HO(CH2)3, 85, 164-5°; PhCH2, 76, 175-5.5°; p-ClC6H4CH2, 80, 156-7°; o-ClC6H4CH2, 84, 169-70°; m-Cl-C6H4CH2 (VIa), 75, 160-60.5°; p-MeOC6H4CH2, 71, 151.5-2.5°; p-MeC6H4CH2, 73, 156.5-7.5°; p-iso-PrC6H4CH2, 80, 175-6°; PhCH2CH2, 70, 148.5-9.5°; HCO, 75, 107-10; EtO2C (VIb), 84, 178-9°; Ac, 88, 174.5-6.5°; Bz, 80, 155-6°. O-Acylation gave VII (Z = Ac or Bz) (R and m.p. of acetate and of benzoate given): PhCH2, 153-4°, 148-9.5°; p-ClC6H4CH2, 145-7°, 155-7°; o-ClC6H4CH2, 158-9°, 141-2°; m-ClC6H4CH2, 152-3°, 139.5-40°; p-MeC6H4CH2, -, 122-3°; p-iso-PrC6H4-CH2, 134-5°, 90.5-1.5°; PhCH2CH2, 133-4°, 155.5-6.5°; EtO2C, 128-9°, 176-7°. Piperazine hexahydrate (33 g.) and 5.9 g. K2CO3 in 200 ml. EtOH treated at reflux over 2 hrs. with 24.5 g. III, clarified, and treated with p-MeC6H4SO3H (Ts) gave 80% IV.2Ts (R = H) (IVb), m. 223-4°, and 15% VIII.2Ts (Y = CH2CH2), m. 289-90°. Also prepared were 81% VI.2Ts (R = H) (VIc), m. 250-1.5°, and 10% VIII.2Ts (Y = CH2CHOHCH2), m. 274-6°, converted to VIII.2Ts (Y = CH2CHOAcCH2), m. 264-5°. IVa was also prepared in 70 or 75% yield by heating II, I (R = PhCH2, X = CH2CH2Cl), and K2CO3 in EtOH or by heating IVb, PhCH2Cl, and Et3N in EtOH, resp. Similar alkylation of VIc gave 79% VIa or the following VI (R, % yield, and m.p. given): α-naphthylmethyl, 62, – (2HCl salt, m. 272-4°); 2-pyridylethyl, 76 (heated with 2-vinylpyridine and AcOH in EtOH), 169.5-70.5°. Hydrolysis of VIb in 35% HBr-AcOH 4 hrs. at 60° also gave 90% VIc. Similarly, hydrolysis with concentrated HCl 20-5 hrs. at reflux removed Ac and Bz groups and gave 68-75% VIc. In the experiment, the researchers used many compounds, for example, 1-Propylpiperazine (cas: 21867-64-1Application of 21867-64-1).
1-Propylpiperazine (cas: 21867-64-1) belongs to piperazine derivatives. Piperazine is a fairly basic compound and is an amine solvent. Intermediate for a wide range of pharmaceuticals, polymers, dyes, corrosion inhibitors, rubber accelerators and surfactants.Application of 21867-64-1
Referemce:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics