Methanol → Methyl 4-(piperidin-2-yl)butanoate hydrochloride

HRID 2388714Notes

Reaction equation

HRID 2388714 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12].S(Cl)([Cl:16])=O.[CH3:18]O>>[ClH:16].[NH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[CH2:8][CH2:9][CH2:10][C:11]([O:13][CH3:18])=[O:12]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 124163274-(Piperidin-2-yl)butanoic acid--hydrogen chloride (1/1)

Product 1

HCID 66772062Methyl 4-(piperidin-2-yl)butanoate hydrochlorideYield 45%

Procedure

A solution of 4-(2-piperidinyl)butanoic acid hydrochloride (5.95 g, 34.8 mmol) in Methanol (104 ml) is cooled to 0° C. At this temperature thionylchloride (7.54 ml, 104.3 mmol) is added slowly. The reaction mixture is heated to reflux for 12 h. The solvent is evaporated in vacuum. The residue is suspended in ethylacetate and is heated to reflux. The suspension is filtered while it is still hot. In the filtrate a white solid dropped out, which was filtered out and dried in vacuum to give Methyl 4-(piperidin-2-yl)butanoate hydrochloride (2) (3.49 g, 45%)

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 12 h
  3. customThe solvent is evaporated in vacuum
  4. temperatureis heated to reflux
  5. filtrationThe suspension is filtered while it
  6. additionIn the filtrate a white solid dropped out
  7. filtrationwhich was filtered out
  8. customdried in vacuum

Sources & evidence

ORD record
ord-ad4ac774d20e456bbb3b96e11797832c
Source dataset
uspto-grants-2012_09
Patent number
US08268814B2

Reaction notes

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