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

HRID 1666168Notes

Reaction equation

HRID 1666168 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-2a88233a08604ed4b36afcfa1ab98a1c
Source dataset
uspto-grants-2011_10
Patent number
US08044046B2

Reaction notes

Loading…