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

HRID 1881683Notes

Reaction equation

HRID 1881683 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) was cooled to 0° C. Thionyl chloride (7.54 ml, 104.3 mmol) was slowly added at this temperature. The reaction mixture was heated under reflux for 12 h. The solvent was evaporated off under reduced pressure. The residue was suspended in ethyl acetate and the suspension was heated under reflux. The suspension was filtered hot. A white precipitate precipitates out in the filtrate, and was filtered out and dried under reduced pressure to give the product methyl 4-(piperidine-2-yl)butanoate hydrochloride (2) (3.49 g, 45%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 12 h
  3. customThe solvent was evaporated off under reduced pressure
  4. temperaturethe suspension was heated
  5. temperatureunder reflux
  6. filtrationThe suspension was filtered hot
  7. customA white precipitate precipitates out in the filtrate
  8. filtrationwas filtered out
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-1bfeece9c79545f4ba90cda4d6079ccd
Source dataset
uspto-grants-2012_11
Patent number
US08318769B2

Reaction notes

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