Hydrochloric Acid → 4-(3-Piperidin-1-ylpropoxy)benzoic acid hydrochloride

HRID 268706

Reaction equation

HRID 268706 reaction equation
[N:1]1([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:21]=[CH:20][C:14]([C:15]([O:17]CC)=[O:16])=[CH:13][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[ClH:22]>>[ClH:22].[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:20][CH:21]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 17986307Ethyl 4-(3-Piperidin-1-ylpropoxy)benzoate

Product 1

HCID 689636144-(3-Piperidin-1-ylpropoxy)benzoic acid hydrochloride

Procedure

A solution of ethyl 4-(3-piperidin-1-ylpropoxy)benzoate (D1) (82.57 g) in concentrated hydrochloric acid (750 ml) was heated under reflux for 2 h. The mixture was cooled to rt then chilled to 5° C. and filtered. The filter cake was washed with acetone and dried to yield the title compound (D2) as a white crystalline solid (75.30 g) that displayed MS and 1H NMR spectra that were identical to those of the product obtained by D2 (Method A).

Workup

  1. temperatureunder reflux for 2 h
  2. temperaturethen chilled to 5° C.
  3. filtrationfiltered
  4. washThe filter cake was washed with acetone
  5. customdried

Sources & evidence

ORD record
ord-fee1f30b78e144288854b0842b1d65b0
Source dataset
uspto-grants-2008_11
Patent number
US07446103B2

Linked notes

Loading…