Benzophenone imine → HCID 66939208, compound

HRID 1716893Notes

Reaction equation

HRID 1716893 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12](Br)[C:11]=2[F:17])[CH2:4][CH2:3]1.C(=[NH:31])(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.CO.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].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>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([NH2:31])[C:11]=2[F:17])[CH2:4][CH2:3]1

Participants

8

Reactant 3

HCID 136809Benzophenone imineHCID 23676156Sodium t-butoxideHCID 66938504HCID 66938504, compound

Product 1

HCID 66939208HCID 66939208, compoundYield 133%

Reagents, catalysts & solvents 4

HCID 634876Binap, (A+-)-CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

Mix 1-methyl-4-(N-(2-fluoro-3-bromophenyl)methylamino)piperidine (Preparation 24, 0.42 g), benzophenone imine (0.303 g), Pd2(dba)3 (25 mg), racemic BINAP (35 mg) and sodium t-butoxide (0.187 g) in toluene (10 mL) and heat at reflux for 3 hours. Dilute the reaction mixture with methanol (5 mL), load on a SCX column (10 g), wash with methanol, elute the with 2M NH3 in methanol, evaporate and further purify on a silica gel column (10 g), using a gradient of dichloromethane-2M NH3 in methanol to give 0.44 g of the title intermediate.

Workup

  1. temperatureheat
  2. temperatureat reflux for 3 hours
  3. washwash with methanol
  4. washelute the with 2M NH3 in methanol
  5. customevaporate
  6. customfurther purify on a silica gel column (10 g)

Sources & evidence

ORD record
ord-fa63db8b7a9b4951a912e8cbfb022b9d
Source dataset
uspto-grants-2010_09
Patent number
US07803813B2

Reaction notes

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