Toluene → HCID 54593439, compound

HRID 1821978Notes

Reaction equation

HRID 1821978 reaction equation
Br[CH:2]1CCC[CH2:4][N:3]1OC1C=CC=CC=1.C(=[NH:28])(C1C=CC=CC=1)C1C=CC=CC=1.C[C:30]([CH3:33])([O-:32])[CH3:31].[Na+].[C:35]1(C)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[NH:3]1[CH2:4][CH2:33][CH:30]([O:32][C:37]2[CH:36]=[C:35]([NH2:28])[CH:40]=[CH:39][CH:38]=2)[CH2:31][CH2:2]1

Participants

6

Reactant 4

HCID 1140TolueneHCID 136809Benzophenone imineHCID 23676156Sodium t-butoxideHCID 69070494HCID 69070494, compound

Product 1

HCID 54593439HCID 54593439, compound

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

Next, the bromophenoxypiperidine intermediate is aminated at the benzo 3-position, as for example, by reacting the intermediate with (±)BINAP, Pd2(dba)3, benzhydrylideneamine, and sodium tertbutoxide in a suitable solvent, such as toluene or the like, under an inert atmosphere for about 1 to about 3 hrs., say about 2 hours, at about 50° C. to 100° C., say about 80° C. The resulting 3-(piperidin-4-yloxy)-phenylamine intermediate may then be isolated and purified by common procedures such as, but not limited to, solvent removal, extraction, and/or chromatography, etc.

Workup

  1. customsay about 80° C

Sources & evidence

ORD record
ord-25fea246d80d4476afef585af30da1ee
Source dataset
uspto-grants-2009_10
Patent number
US07608629B2

Reaction notes

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