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

HRID 267337노트

반응식

HRID 267337 반응식
ICCCC(OC)=O.N1CCCC1.[N:14]1([CH2:19][CH2:20][CH2:21][C:22]([O:24]C)=[O:23])[CH2:18][CH2:17][CH2:16][CH2:15]1.[ClH:26]>C1C=CC=CC=1>[ClH:26].[N:14]1([CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23])[CH2:18][CH2:17][CH2:16][CH2:15]1

참가 물질

6

반응물 4

HCID 313Hydrochloric Acid2회HCID 30905Methyl 1-pyrrolidinebutanoateHCID 31268PyrrolidineHCID 547991Methyl 4-iodobutanoate

생성물 1

HCID 148556824-(Pyrrolidin-1-yl)butanoic acid hydrochloride

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

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.

후처리

  1. customA dark orange layer formed
  2. customThe benzene solution was decanted
  3. concentrationconcentrated
  4. distillationdistilled (b.p. 100°C. at 15 mm Hg)
  5. customto give 10 g
  6. dissolutionThis material was dissolved in 100 ml
  7. temperatureat reflux for 28 hours
  8. concentrationThe solution was concentrated under reduced pressure
  9. customto give a semi-solid which
  10. customwas triturated with acetone
  11. filtrationfiltered
  12. customRecrystallization from acetic acid/acetone
  13. customgave 8.3 g

출처 및 근거

ORD 기록
ord-b00d8a8b1c5a4db6b5fb77312f4b98e6
출처 데이터셋
uspto-grants-1976_03
특허 번호
US03941782

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