Piperidine → HCID 54591672, compound

HRID 509261Notes

Reaction equation

HRID 509261 reaction equation
Br[C:2]1[N:7]=[C:6]([C:8]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]2[C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)=[O:9])[CH:5]=[CH:4][CH:3]=1.[NH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.CC(C)([O-])C.[Na+].[Cl-].[NH4+]>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>[N:22]1([C:2]2[N:7]=[C:6]([C:8]([N:10]3[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]3[C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)=[O:9])[CH:5]=[CH:4][CH:3]=2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

8

Reactant 4

HCID 8082PiperidineHCID 25517Ammonium ChlorideHCID 23676156Sodium t-butoxideHCID 86692072HCID 86692072, compound

Product 1

HCID 54591672HCID 54591672, compoundYield 64.3%

Reagents, catalysts & solvents 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

(6-bromopyridin-2-yl)(2-(pyridin-3-yl)piperidin-1-yl)methanone (60 mg, 0.173 mmol), piperidine (18 mg, 0.208 mmol), Pd2(dba)3 (3 mg, 0.003 mmol), xantphos (6 mg, 0.010 mmol), and sodium-tert-butoxide (25 mg, 0.260 mmol) were suspended in toluene (3 ml), and then stirred at 100° C. under nitrogen stream for 3 hours. A saturated aqueous ammonium chloride solution of (15 ml) was added to the resulting reaction liquid, followed by extraction with MC (15 ml×2). The organic layer was dried over anhydrous magnesium sulfate, followed by filtration and concentration, and then the residue thus obtained was subjected to MPLC (90% EtOAc/Hexanes), to obtain 39 mg of pale yellow oil (64%). MS (ESI): 351 [M+H]+

Workup

  1. extractionfollowed by extraction with MC (15 ml×2)
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfollowed by filtration and concentration
  4. customthe residue thus obtained

Sources & evidence

ORD record
ord-7c2b78d21f7d40ceb8acea7d69c1e34e
Source dataset
uspto-grants-2015_08
Patent number
US09096571B2

Reaction notes

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