Hydrochloric Acid → (3-Amino-5-(trifluoromethyl)phenyl)(1-methylpiperidin-4-yl)methanone

HRID 2200132Notes

Reaction equation

HRID 2200132 reaction equation
C1(C(=[N:14][C:15]2[CH:16]=[C:17]([C:25]([CH:27]3[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]3)=[O:26])[CH:18]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:20]=2)C2C=CC=CC=2)C=CC=CC=1.Cl.CCOC(C)=O>C1COCC1>[NH2:14][C:15]1[CH:16]=[C:17]([C:25]([CH:27]2[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]2)=[O:26])[CH:18]=[C:19]([C:21]([F:22])([F:23])[F:24])[CH:20]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 118223414(3-(Diphenylmethyleneamino)-5-(trifluoromethyl)phenyl)(1-methylpiperidin-4-yl)methanone

Product 1

HCID 118223409(3-Amino-5-(trifluoromethyl)phenyl)(1-methylpiperidin-4-yl)methanoneYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve (3-(diphenylmethyleneamino)-5-(trifluoromethyl)phenyl)(1-methylpiperidin-4-yl)methanone (210 mg, 0.47 mmol) in THF (2 mL) in an ice-bath, add hydrochloric acid (4N, 0.5 mL), then stir it at room temperature for one hour. TLC (PE:EtOAc=1:1) shows the reaction is complete. Partition the mixture between EtOAc and water. Collect the aqueous layer, adjust pH=9 with sodium hydroxide solution, extract with ethyl acetate three times, combine the organic layers, dry over anhydrous sodium sulfate, concentrate to yield the crude product (78 mg, 59%). MS: (M+1): 287.1.

Workup

  1. customPartition the mixture between EtOAc and water
  2. customCollect the aqueous layer
  3. extractionextract with ethyl acetate three times
  4. dry with materialdry over anhydrous sodium sulfate
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-08d24c29d9f44855863413fb253cc561
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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