Hydrochloric Acid → 7-fluoro-1,1-dimethyl-2,3-dihydro-1H-inden-5-amine

HRID 2202228Notes

Reaction equation

HRID 2202228 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:13]=C(C2C=CC=CC=2)C2C=CC=CC=2)[CH:5]=[C:6]2[C:10]=1[C:9]([CH3:12])([CH3:11])[CH2:8][CH2:7]2.Cl.[OH-].[Na+]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([NH2:13])[CH:5]=[C:6]2[C:10]=1[C:9]([CH3:11])([CH3:12])[CH2:8][CH2:7]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 118622697N-(7-fluoro-1,1-dimethyl-2,3-dihydro-1H-inden-5-yl)-1,1-diphenylmethanimine

Product 1

HCID 1186227997-fluoro-1,1-dimethyl-2,3-dihydro-1H-inden-5-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the crude N-(7-fluoro-1,1-dimethyl-2,3-dihydro-1H-inden-5-yl)-1,1-diphenylmethanimine in THF (30 mL) was added LM hydrochloric acid (29 mL, 29.17 mmol) at room temperature, and the mixture was stirred at room temperature for 30 min. The pH of the reaction mixture was adjusted to >7 with sodium hydroxide, and the mixture was extracted with ethyl acetate (×2). The organic layer was washed with 10% brine, dried over sodium sulfate, and concentrated under reduced pressure to give the crude 7-fluoro-1,1-dimethyl-2,3-dihydro-1H-inden-5-amine as an orange oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (×2)
  2. washThe organic layer was washed with 10% brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3e061d1996a24c4db2786e7c65ac203f
Source dataset
uspto-grants-2016_06
Patent number
US09365520B2

Reaction notes

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