Hydrochloric Acid → 4-(4-Morpholinylmethyl)benzoic acid hydrochloride

HRID 1192759Notes

Reaction equation

HRID 1192759 reaction equation
C[O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[CH:6][CH:5]=1.[OH-].[Na+].[Na+].[Cl-:21].Cl>O>[Cl-:21].[C:3]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][NH+:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[CH:8][CH:9]=1)([OH:17])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 10466592Methyl 4-(morpholin-4-ylmethyl)benzoate

Product 1

HCID 866216114-(4-Morpholinylmethyl)benzoic acid hydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 200 mL round-bottom flask was charged with 4-morpholin-4-ylmethyl-benzoic acid methyl ester (4.0 g, 0.017 mol, 1.0 eq). A solution of NaOH (2.0 g, 0.051 mol, 3.0 eq) in water was added and the reaction mixture was stirred overnight at room temperature. NaCl (5.0 g) and HCl (6.0 M in water, 17 mL, 6.0 eq) were then added. The reaction mixture was cooled to 0° C. and then stirred for 1 hr. The solid was collected by filtration, washed with pentane and dried at 50° C. under vacuum to yield the title compound as a white solid.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. stirringstirred for 1 hr
  3. filtrationThe solid was collected by filtration
  4. washwashed with pentane
  5. customdried at 50° C. under vacuum

Sources & evidence

ORD record
ord-c082bdcf3fc54896a365df8c30001e51
Source dataset
uspto-grants-2014_03
Patent number
US08680273B2

Reaction notes

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