Hydrochloric Acid → 1-(4-Fluoro-3-methylphenyl)-2-methylpropan-2-amine

HRID 506555Notes

Reaction equation

HRID 506555 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:12]C=O)([CH3:11])[CH3:10])=[CH:4][C:3]=1[CH3:15].Cl.[OH-].[Na+]>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH2:12])([CH3:10])[CH3:11])=[CH:4][C:3]=1[CH3:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22063477HCID 22063477, compound

Product 1

HCID 220634761-(4-Fluoro-3-methylphenyl)-2-methylpropan-2-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

4.3 g (20.6 mmol) of N-[2-(4-fluoro-3-methylphenyl)-1,1-dimethylethyl]formamide, 20 mL concentrated hydrochloric acid, and 20 mL water are refluxed for 2 hours. The reaction mixture is diluted with water, made alkaline with concentrated sodium hydroxide solution, and extracted with dichloromethane. The organic phases are dried with sodium sulfate and evaporated down. The residue is dissolved in ethyl acetate, combined with ethereal hydrochloric acid, and cooled. The crystals precipitated are suction filtered and washed with diethyl ether and dried. White solid. Yield: 3.9 g (87%, hydrochloride); melting point 196° C.-198° C.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic phases are dried with sodium sulfate
  3. customevaporated down
  4. dissolutionThe residue is dissolved in ethyl acetate
  5. temperaturecooled
  6. customThe crystals precipitated
  7. filtrationare suction filtered
  8. washwashed with diethyl ether
  9. customdried

Sources & evidence

ORD record
ord-7c38694f33594d41b8d0446364b88b8e
Source dataset
uspto-grants-2010_08
Patent number
US07786111B2

Reaction notes

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