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

HRID 1258443Notes

Reaction equation

HRID 1258443 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-c8a6885ab1e54b8b9cf0ea3e834c4ee2
Source dataset
uspto-grants-2013_06
Patent number
US08466165B2

Reaction notes

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