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

HRID 500696Notes

Reaction equation

HRID 500696 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-1925649bad4e4201952544b59341bbf5
Source dataset
uspto-grants-2010_08
Patent number
US07772243B2

Reaction notes

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