Hydrochloric Acid → 4-(Pyrrolidin-1-yl)butanoic acid hydrochloride

참여 물질

반응 단계

30.0 g. (0.13 mole) of Methyl γ-iodobutyrate (Blicke et al., J. Am. Chem. Soc. 63, 2488 (1941)) was combined with 36 g. of pyrrolidine in 300 ml. of benzene, heated at 60°C. for 0.5 hour and stirred at room temperature for 16 hours. A dark orange layer formed. The benzene solution was decanted, concentrated and distilled (b.p. 100°C. at 15 mm Hg) to give 10 g. of colorless liquid. The infrared and nuclear magnetic resonance spectra indicated the product to be methyl γ-pyrrolidino-butyrate. This material was dissolved in 100 ml. of 18% hydrochloric acid and heated at reflux for 28 hours. The solution was concentrated under reduced pressure to give a semi-solid which was triturated with acetone and filtered. Recrystallization from acetic acid/acetone gave 8.3 g. (33%) of the desired acid hydrochloride as colorless crystals, m.p. 126°-127°C. The infrared and nuclear magnetic resonance spectra were consistent with the proposed structure.

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