Hydrochloric Acid → HCID 66939006, compound

HRID 1716895Notes

Reaction equation

HRID 1716895 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([NH:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13](Cl)[C:12]=2[F:18])[CH2:4][CH2:3]1.C(=[NH:32])(C1C=CC=CC=1)C1C=CC=CC=1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.CC(C)([O-])C.[Na+].Cl>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]>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([NH:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([NH2:32])[C:12]=2[F:18])[CH2:4][CH2:3]1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 136809Benzophenone imineHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 23676156Sodium t-butoxideHCID 66938866HCID 66938866, compound

Product 1

HCID 66939006HCID 66939006, compoundYield 11.4%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

Mix 1-methyl-4-(N-(2-fluoro-3-chlorophenyl)ethylamino)piperidine (Preparation 26) (0.367 g), benzophenone imine (0.295 g), Pd2 (dba)3 (50 mg), 2-(di-t-butylphosphino)biphenyl (32 mg), and sodium t-butoxide (0.182 g) in toluene (10 mL) and heat at reflux for three days. Dilute with methanol (5 mL), 30 minutes after adding 2 mL of 5N HCl, load on a SCX column (10 g), wash with methanol, elute the product with 2M NH3 in methanol, evaporate and purify on a silica gel column (35 g), using a gradient of dichloromethane-2M NH3 in methanol to give 39 mg of the title compound: mass spectrum (electric spray) m/z=252 (M+1).

Workup

  1. temperatureheat
  2. temperatureat reflux for three days
  3. washwash with methanol
  4. washelute the product with 2M NH3 in methanol
  5. customevaporate
  6. custompurify on a silica gel column (35 g)

Sources & evidence

ORD record
ord-763497453ff7464c89c41284f79b37d4
Source dataset
uspto-grants-2010_09
Patent number
US07803813B2

Reaction notes

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