Hydrochloric Acid → HCID 67110183, compound

HRID 2381236Notes

Reaction equation

HRID 2381236 reaction equation
[CH3:1]N(C)C=O.[CH2:6]([O:13][C:14]1[C:15]([O:29][CH3:30])=[CH:16][C:17](I)=[C:18]([C:20]([N:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[O:21])[CH:19]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C]=O.Cl.[C:34]([O:37][CH2:38][CH3:39])(=[O:36])C>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].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C(N(CC)CC)C.CC(O)C>[CH2:6]([O:13][C:14]1[C:15]([O:29][CH3:30])=[CH:16][C:17]([C:34]([O:37][CH:38]([CH3:39])[CH3:1])=[O:36])=[C:18]([C:20]([N:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[O:21])[CH:19]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 58345609HCID 58345609, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 67110183HCID 67110183, compound

Reagents, catalysts & solvents 4

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 3776IsopropanolSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of tris(dibenzylideneacetone)dipalladium(0) (157 mg), 1,1′-bis(diphenylphosphino)ferrocene (380 mg) and N,N-dimethylformamide (10 mL) was stirred under an argon atmosphere for 10 minutes. To the mixture were added (5-benzyloxy-2-iodo-4-methoxyphenyl)piperidin-1-yl-methanone (reference example 6-1) (1.55 g), 2-propanol (10 mL) and triethylamine (1.44 mL). After displacement to a carbon monoxide atmosphere, the mixture was stirred at 90° C. for 14 hours. After cooling to room temperature, to the mixture were added ethyl acetate and 2 mol/L hydrochloric acid. The separated organic layer was washed with water, a 2 mol/L aqueous solution of sodium hydroxide, an aqueous solution of sodium bicarbonate and brine successively, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: 15%-45% ethyl acetate/hexane, gradient elution) to give the title compound (258 mg).

Workup

  1. washThe separated organic layer was washed with water
  2. dry with materiala 2 mol/L aqueous solution of sodium hydroxide, an aqueous solution of sodium bicarbonate and brine successively, dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (eluent: 15%-45% ethyl acetate/hexane, gradient elution)

Sources & evidence

ORD record
ord-42f18f01e0ec4bc3b76a8d6bb0f8d926
Source dataset
uspto-grants-2012_09
Patent number
US08258162B2

Reaction notes

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