Hydrochloric Acid → 2-Methyl-4-piperidin-1-yl-butyric acid hydrochloride

HRID 1657657Notes

Reaction equation

HRID 1657657 reaction equation
[CH3:1][CH:2]([CH2:8][CH2:9][N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)[C:3]([O:5]CC)=[O:4].[ClH:16]>O>[ClH:16].[CH3:1][CH:2]([CH2:8][CH2:9][N:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1)[C:3]([OH:5])=[O:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 20361120Ethyl 2-methyl-4-piperidinobutyrate

Product 1

HCID 211526892-Methyl-4-piperidin-1-yl-butyric acid hydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6.5 g. (0.030 mole) of ethyl 2-methyl-4-piperidinobutyrate was combined with a mixture of 45 ml. of water and 45 ml. of concentrated hydrochloric acid and heated at reflux for 16 hours. The solution was concentrated under reduced pressure (water aspirator) to give a residue which crystallized upon addition of 50 ml. of diethyl ether. The ether was decanted, and the solid was triturated with acetone and filtered. Recrystallization from acetic acid/acetone gave 3.38 g. of colorless crystals, m.p. 166°-168°C. and a second crop of 1.27 g. of solid, m.p. 165°-168°C. The total yield for both batches was 69%. Anal. Calcd. for C10H20ClNO2 (MW = 221.72): C, 54.20; H, 9.09; N, 6.32; Found: C, 54.17; H, 9.15; N, 6.36.

Workup

  1. temperatureat reflux for 16 hours
  2. concentrationThe solution was concentrated under reduced pressure (water aspirator)
  3. customto give a residue which
  4. customcrystallized upon addition of 50 ml
  5. customThe ether was decanted
  6. customthe solid was triturated with acetone
  7. filtrationfiltered
  8. customRecrystallization from acetic acid/acetone
  9. customgave 3.38 g
  10. customThe total yield for both batches

Sources & evidence

ORD record
ord-722d43eaa56443928c7beba2bdbd8f36
Source dataset
uspto-grants-1976_06
Patent number
US03960871

Reaction notes

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