Hydrochloric Acid → 4-Morpholin-4-yl-3-(trifluoromethyl)benzoic acid

HRID 1465023Notes

Reaction equation

HRID 1465023 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:14]=[CH:13][C:10]([C:11]#N)=[CH:9][C:8]=2[C:15]([F:18])([F:17])[F:16])[CH2:3][CH2:2]1.[OH-:19].[Na+].Cl.O1CCCC1.C[OH:28].O>>[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:14]=[CH:13][C:10]([C:11]([OH:28])=[O:19])=[CH:9][C:8]=2[C:15]([F:18])([F:17])[F:16])[CH2:3][CH2:2]1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21892291Methanol tetrahydrofuran waterHCID 595565444-Morpholino-3-(trifluoromethyl)benzonitrile

Product 1

HCID 594957964-Morpholin-4-yl-3-(trifluoromethyl)benzoic acid

Procedure

4-Morpholino-3-(trifluoromethyl)benzonitrile (2.1 g, 8.016 mmol) was dissolved in a mixture of tetrahydrofurane/methanol/water (1:1:1, v/v/v, 20 mL), sodium hydroxide (1.9 g, 48.10 mmol) was added thereto and stirred for 40 hours with reflux. The reaction mixture was cooled to room temperature and 1N hydrochloride was added slowly thereto to pH 3˜4. The resulting solid was filtered, washed with water and dimethyl ether and then dried to obtain the title compound (694 mg).

Workup

  1. additionwas added
  2. temperaturewith reflux
  3. filtrationThe resulting solid was filtered
  4. washwashed with water and dimethyl ether
  5. customdried

Sources & evidence

ORD record
ord-858d4b4f6e35483d9c5f87124b0121d1
Source dataset
uspto-grants-2015_04
Patent number
US08999973B2

Reaction notes

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