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

HRID 1679515Notes

Reaction equation

HRID 1679515 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 (4.96g) 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 (3.7g), 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-5f53e204209543cb8271d32f51de3b50
Source dataset
uspto-grants-1978_03
Patent number
US04080335

Reaction notes

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