Hydrochloric Acid → HCID 58997309, compound

HRID 1716877Notes

Reaction equation

HRID 1716877 reaction equation
Br[C:2]1[CH:3]=[C:4]([N:9]([CH3:17])[CH:10]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)[CH:5]=[C:6]([F:8])[CH:7]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C(=[NH:77])(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[Na+].Cl>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1COCC1.C1(C)C=CC=CC=1>[F:8][C:6]1[CH:7]=[C:2]([NH2:77])[CH:3]=[C:4]([N:9]([CH3:17])[CH:10]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)[CH:5]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 136809Benzophenone imineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 58997315HCID 58997315, compound

Product 1

HCID 58997309HCID 58997309, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

The (3-bromo-5-fluorophenyl)-methyl-(1-methylpiperidin-4-yl)-amine intermediate is then aminated at the benzo 3-position, as for example, by reacting the intermediate with BINAP, Pd2dba3, benzhydrylideneamine, and sodium t-butoxide, in a suitable solvent, such as toluene or the like, under an inert atmosphere for about 1-3 hr., say about 2 hr., at about 50° C. to 100° C., say about 80° C. The resulting intermediate is treated with 1M HCl or the like in a suitable solvent, such as THF at 0° C. to ambient temperature, preferably ambient temperature for 1-2 hours, say about 1 hr. The resulting intermediate, 5-fluoro-N-methyl-N-(1-methylpiperidin-4-yl)benzene-1,3-diamine may then be isolated and purified by common procedures such as, but not limited to, solvent removal, extraction and/or chromatography, etc.

Workup

  1. customat about 50° C. to 100° C.
  2. customsay about 80° C
  3. waitsay about 1 hr

Sources & evidence

ORD record
ord-8c284b14a9df4a5284e917e027e583eb
Source dataset
uspto-grants-2010_09
Patent number
US07803813B2

Reaction notes

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