Hydrochloric Acid → 4-Piperidin-1-yl-but-2-enoic acid-HCl

HRID 467604Notes

Reaction equation

HRID 467604 reaction equation
C[O:2][C:3](=[O:13])[CH:4]=[CH:5][CH2:6][N:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.[ClH:14]>>[ClH:14].[N:7]1([CH2:6][CH:5]=[CH:4][C:3]([OH:13])=[O:2])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 572293064-Piperidin-1-yl-but-2-enoic acid methyl ester

Product 1

HCID 698441674-Piperidin-1-yl-but-2-enoic acid-HClYield 17%

Procedure

4-Piperidin-1-yl-but-2-enoic acid methyl ester (2.05 g, 11.2 mmol) and concentrated hydrochloric acid (10 mL) were combined in dioxanes (30 mL) and heated to reflux overnight. The mixture was concentrated in vacuo. The residue was crystallized from IPA to yield the desired product (390 mg, 17%). 400 MHz 1H NMR (DMSO-d6) δ 6.80 (dt, 1H, J=15.6, 7.1 Hz), 6.14 (d, 1H, J=15.6 Hz), 3.85 (d, 1H, J=7.1 Hz), 2.89 (m, 4H), 1.54 (m, 6H). MS m/z 170 (M+1).

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. concentrationThe mixture was concentrated in vacuo
  4. customThe residue was crystallized from IPA

Sources & evidence

ORD record
ord-04ac8d251b934e5ebf7ed767bda7eb9f
Source dataset
uspto-grants-2014_01
Patent number
US08623883B2

Reaction notes

Loading…