Methanol → 5-Fluoro-N,N-dimethyl-2,3,4,9-tetrahydro-1H-carbazol-3-amine

HRID 461556Notes

Reaction equation

HRID 461556 reaction equation
[CH3:1][N:2]([CH3:18])[CH:3]1[CH2:15][C:14]2[C:13]3[C:8](=[C:9](Br)[CH:10]=[CH:11][C:12]=3[F:16])[NH:7][C:6]=2[CH2:5][CH2:4]1.CO.[OH-].[K+]>[Pd].O>[CH3:1][N:2]([CH3:18])[CH:3]1[CH2:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][C:12]=3[F:16])[NH:7][C:6]=2[CH2:5][CH2:4]1

Participants

6

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 12891793HCID 12891793, compound

Product 1

HCID 123618445-Fluoro-N,N-dimethyl-2,3,4,9-tetrahydro-1H-carbazol-3-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

Following a procedure similar to that described in Example 234 but using 2 g. of 3-(dimethylamino)-8-bromo-5-fluoro-1,2,3,4-tetrahydrocarbazole (Example 219), in 100 ml. of methyl alcohol, 1 g. of 10% palladium on charcoal and 1 g. of potassium hydroxide in 2 ml. of water there was obtained, after recrystallization from benzene, 1.3 g. of 3-(dimethylamino)-5-fluoro-1,2,3,4-tetrahydrocarbazole, m.p. 166°-168° C.

Workup

  1. customafter recrystallization from benzene, 1.3 g

Sources & evidence

ORD record
ord-f261f4df40f1402cb5e4344025d36d8a
Source dataset
uspto-grants-1977_12
Patent number
US04062864

Reaction notes

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