Hydrochloric Acid → 4-[3-(dibutylamino)propoxy]benzoic Acid Hydrochloride

HRID 971083Notes

Reaction equation

HRID 971083 reaction equation
[CH2:1]([N:5]([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16]C)=[O:15])=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH3:4].[ClH:24]>>[ClH:24].[CH2:20]([N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([OH:16])=[O:15])=[CH:12][CH:11]=1)[CH2:21][CH2:22][CH3:23]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 9836814Methyl 4-(3-(dibutylamino)propoxy)benzoate

Product 1

HCID 102690134-[3-(dibutylamino)propoxy]benzoic Acid HydrochlorideYield 85.7%

Procedure

A mixture of methyl 4-(3-dibutylaminopropoxy)benzoate [18a] (7.65 g, 23.8 mmol) and 32% hydrochloric acid (30 mL) was stirred for 5 hours under reflux conditions and for one hour at 0-5° C. (ice/water bath). The suspension was filtered. The precipitated crystals were washed on the filter with water and hexane and dried under reduced pressure at 50-60° C. (water bath) to give 6.90 g (85.7%) of 4-(3-dibutylaminopropoxy)benzoic acid hydrochloride [19a] as white crystals with mp 157-159° C.

Workup

  1. filtrationThe suspension was filtered
  2. washThe precipitated crystals were washed on the
  3. filtrationfilter with water and hexane
  4. dry with materialdried under reduced pressure at 50-60° C. (water bath)

Sources & evidence

ORD record
ord-4b7508136c954d778bfdf881b561493d
Source dataset
uspto-grants-2007_12
Patent number
US07312345B2

Reaction notes

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