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

HRID 2071975ノート

反応式

HRID 2071975 の反応式
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

参加物

6

反応物 4

HCID 313Hydrochloric Acid2 回HCID 30905Methyl 1-pyrrolidinebutanoateHCID 31268PyrrolidineHCID 547991Methyl 4-iodobutanoate

生成物 1

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

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

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 hours 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 mmHg) to give 10 g. of colorless liquid. The infrared and nmr spectra indicated the 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 semisolid 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 and consistent with the proposed structure.

後処理

  1. customA dark orange layer formed
  2. customThe benzene solution was decanted
  3. concentrationconcentrated
  4. distillationdistilled (b.p. 100° at 15 mmHg)
  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 semisolid which
  10. customwas triturated with acetone
  11. filtrationfiltered
  12. customRecrystallization from acetic acid/acetone
  13. customgave 8.3 g

出典と根拠

ORDレコード
ord-55e833ad059b4bea8342b9a715f1d4fc
出典データセット
uspto-grants-1977_09
特許番号
US04049653

反応ノート

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