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

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Reaction Steps

30.0 g. (0.13 mole) of Methyl γ-iodobutyrate (F.F. Blicke, W.B. Wright and M.F. Zienty, J. Amer. Chem. Soc. 63, 2488 (1941) was combined with 36 g. of pyrrolidine (Aldrich) in 300 ml. of benzene, heated at 60° 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° at 15 mm Hg) to give 10 g. of colorless liquid. The infrared and nmr spectra indicated that product to be methyl Γ-pyrrolidinobutyrate. 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°. The infrared and nmr spectra are consistent with the proposed structure.

Provenance & Evidence