Pyrrolidine, 1-(2-(4-(2,2-dimethyl-7-methoxy-3-phenyl-2H-1-benzopyran-4-yl)phenoxy)ethyl)- → HCID 10895762, compound

HRID 582820Notes

Reaction equation

HRID 582820 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][N:30]4[CH2:34][CH2:33][CH2:32][CH2:31]4)=[CH:23][CH:22]=3)=[C:8]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:9]([CH3:14])([CH3:13])[O:10]2)=[CH:5][CH:4]=1.[H][H]>C(O)(=O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C@H:7]([C:21]3[CH:22]=[CH:23][C:24]([O:27][CH2:28][CH2:29][N:30]4[CH2:34][CH2:33][CH2:32][CH2:31]4)=[CH:25][CH:26]=3)[C@H:8]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:9]([CH3:14])([CH3:13])[O:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 421182Pyrrolidine, 1-(2-(4-(2,2-dimethyl-7-methoxy-3-phenyl-2H-1-benzopyran-4-yl)phenoxy)ethyl)-HCID 178418361HCID 178418361, compound

Product 1

HCID 10895762HCID 10895762, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

7-Methoxy-2,2-dimethyl-3-phenyl-4-{4-[2-(pyrrolidin-1-yl)ethoxy]phenyl}-3-chromene (1 kg) was dissolved in acetic acid (10 l) by heating to 60° C. Palladium on carbon (10%, 50% wet, 100 g) was added and the mixture hydrogenated at 60° C., 2-3 atmospheres hydrogen pressure for 24 hours. The mixture was cooled down to 40-50° C. and the catalyst filtered off. The filtrate was evaporated in vacuum to an oil. It was dissolved in 2-propanol (4 l) and sodium hydroxide was added (ca. 1.2 l, 36%) in order to adjust the pH of the mixture to 10-11. The solution was seeded at 40-50° C. The mixture was cooled down to ca. 5° C. and the product filtered off and washed with water (3 l) and dried at 50° C. Yield 0.9 kg, 95%.

Workup

  1. temperatureThe mixture was cooled down to 40-50° C.
  2. filtrationthe catalyst filtered off
  3. customThe filtrate was evaporated in vacuum to an oil
  4. dissolutionIt was dissolved in 2-propanol (4 l)
  5. additionsodium hydroxide was added (ca. 1.2 l, 36%) in order
  6. customwas seeded at 40-50° C
  7. temperatureThe mixture was cooled down to ca. 5° C.
  8. filtrationthe product filtered off
  9. washwashed with water (3 l)
  10. customdried at 50° C

Sources & evidence

ORD record
ord-97f00cc8c04e489baa84d6dbf29d6f79
Source dataset
uspto-grants-1999_07
Patent number
US05925771

Reaction notes

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