Hydrochloric Acid → 4-(3-(Piperidin-1-yl)propoxy)benzoic acid

HRID 251444Notes

Reaction equation

HRID 251444 reaction equation
[N:1]1([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17]C)=[O:16])=[CH:13][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].Cl>C(O)C.C(O)C.O>[N:1]1([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:12]=[CH:13][C:14]([C:15]([OH:17])=[O:16])=[CH:19][CH:20]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 9817068Methyl 4-(3-piperidin-1-ylpropoxy)benzoate

Product 1

HCID 176069534-(3-(Piperidin-1-yl)propoxy)benzoic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 19096565Water ethanolSolvent

Conditions

Temperature
28 °C

Procedure

To methyl 4-(3-piperidin-1-ylpropoxy)benzoate ax15 (4.41 g, 15.9 mmol, 1 eq) in ethanol (160 ml) is added a 5 N aqueous solution of sodium hydroxide (9.54 ml, 47.7 mmol, 3 eq) and the mixture is stirred at 60° C. for 4 h and at 28° C. overnight. The mixture is concentrated under vacuum to give a white solid, which is then dissolved in a 1:1 mixture of ethanol/water (100 ml). A solution of 5 N aqueous hydrochloric acid is then added until the pH of the mixture reaches 2-3. The ethanol is then evaporated under vacuum and the mixture filtered to give a white solid. This solid is washed with water and dried under vacuum at 40° C.

Workup

  1. concentrationThe mixture is concentrated under vacuum
  2. customto give a white solid, which
  3. customThe ethanol is then evaporated under vacuum
  4. filtrationthe mixture filtered
  5. customto give a white solid
  6. washThis solid is washed with water
  7. customdried under vacuum at 40° C.

Sources & evidence

ORD record
ord-373daaf8308e498493441f5ee2d4daed
Source dataset
uspto-grants-2011_01
Patent number
US07863450B2

Reaction notes

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