2,2-dimethyl-7-dimethylaminoethyloxy-4-(3-trifluoromethylphenyl)-2H-chromene hydrochloride → Brl 16644

HRID 1863040Notes

Reaction equation

HRID 1863040 reaction equation
[ClH:1].[CH3:2][C:3]1([CH3:29])[CH:12]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)[C:10]2[C:5](=[CH:6][C:7]([O:23][CH2:24][CH2:25][N:26]([CH3:28])[CH3:27])=[CH:8][CH:9]=2)[O:4]1.[H][H]>C(O)C.[Pd]>[ClH:1].[CH3:2][C:3]1([CH3:29])[CH2:12][CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:20])([F:22])[F:21])[CH:14]=2)[C:10]2[C:5](=[CH:6][C:7]([O:23][CH2:24][CH2:25][N:26]([CH3:27])[CH3:28])=[CH:8][CH:9]=2)[O:4]1

Participants

5

Reactant 2

HCID 705737262,2-dimethyl-7-dimethylaminoethyloxy-4-(3-trifluoromethylphenyl)-2H-chromene hydrochlorideHCID 178418361HCID 178418361, compound

Product 1

HCID 42987Brl 16644Yield 74.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2,2-dimethyl-7-dimethylaminoethyloxy-4-(3-trifluoromethylphenyl)-2H-chromene hydrochloride (4.96 g) in ethanol (75 ml) was added 10% palladium on charcoal. The mixture was hydrogenated under hydrogen (1 atmosphere pressure) at ambient temperature (about 18° C.) until no further hydrogen was taken up. The mixture was filtered and the solvent removed from the resulting filtrate under reduced pressure to yield the title compound (3.7 g), m.p. 188°-190° C.

Workup

  1. customwas hydrogenated under hydrogen (1 atmosphere pressure) at ambient temperature
  2. custom(about 18° C.)
  3. filtrationThe mixture was filtered
  4. customthe solvent removed from the resulting filtrate under reduced pressure

Sources & evidence

ORD record
ord-d608fe4a7b5a4d92bc332c122480f323
Source dataset
uspto-grants-1979_09
Patent number
US04167515

Reaction notes

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