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HCID 66744472, compound → HCID 66744159, compound

HRID 505111
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Reaction equation

HRID 505111 reaction equation
C([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[C:22]3[O:21][CH2:20][CH2:19][C:18]=3[CH:17]=[C:16](Br)[CH:15]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1>CCO.Cl.[Pd]>[O:21]1[C:22]2[C:14]([CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)=[CH:15][CH:16]=[CH:17][C:18]=2[CH2:19][CH2:20]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 1

HCID 66744472HCID 66744472, compound

Product 1

HCID 66744159HCID 66744159, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 1-benzyl-4-(5-bromo-2,3-dihydro-benzofuran-7-yl)-1,2,3,6-tetrahydro-pyridine in EtOH and 4N HCl was added 40 wt % of 10% Pd/C catalyst. The reaction flask was charged with H2 (3.5 bar) and then stirred overnight at 50° C. The reaction mixture was filtered over Celite under argon. The solvents were evaporated and the product was partitioned between CH2Cl2 and aq. K2CO3. The organic phase was dried over Na2SO4 and evaporated to give the title compound in 81% yield.

Workup

  1. additionThe reaction flask was charged with H2 (3.5 bar)
  2. filtrationThe reaction mixture was filtered over Celite under argon
  3. customThe solvents were evaporated
  4. customthe product was partitioned between CH2Cl2 and aq. K2CO3
  5. dry with materialThe organic phase was dried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-765690d0e20d4bfba243719867f03c67
Source dataset
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07781436B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes