Hexane → HCID 23153019, compound

HRID 492756Notes

Reaction equation

HRID 492756 reaction equation
[N+:1]([C:4]1[CH:31]=[CH:30][C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]([N:18]3[CH2:23][CH2:22][CH:21]([N:24]4[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]4)[CH2:20][CH2:19]3)=[O:17])[CH:10]=2)=[CH:6][CH:5]=1)([O-])=O.[H][H].CCCCCC>O1CCCC1.CO.C(OCC)C.[C].[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]([N:18]3[CH2:19][CH2:20][CH:21]([N:24]4[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]4)[CH2:22][CH2:23]3)=[O:17])[CH:10]=2)=[CH:30][CH:31]=1

Participants

8

Reactant 3

HCID 8058HexaneHCID 86069247N-[4-(4-Nitrophenoxy)-2-pyridinyl][1,4'-bipiperidine]-1'-carboxamideHCID 178418361HCID 178418361, compound

Product 1

HCID 23153019HCID 23153019, compoundYield 75.4%

Reagents, catalysts & solvents 4

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-(Piperidin-1-yl)piperidine-1-carboxylic acid [4-(4-nitrophenoxy)pyridin-2-yl]amide (121 mg) was dissolved in tetrahydrofuran (3 ml)-methanol (3 ml), and then 10% palladium carbon (61 mg) was added thereto under a nitrogen atmosphere, followed by replacing with hydrogen inside the system and stirring overnight. After replacing with nitrogen inside the system, the reaction mixture was filtered to remove the catalyst, which was washed with ethanol. The filtrate was concentrated under a reduced pressure to give a residue, which was then suspended in diethyl ether (2 ml)-hexane (2 ml). The solid was filtered off and dried under aeration to provide the titled compound (84.8 mg, 75.2%).

Workup

  1. filtrationthe reaction mixture was filtered
  2. customto remove the catalyst, which
  3. washwas washed with ethanol
  4. concentrationThe filtrate was concentrated under a reduced pressure
  5. customto give a residue, which
  6. filtrationThe solid was filtered off
  7. customdried under aeration

Sources & evidence

ORD record
ord-bab1a8e5fead4d83a93cd8af75a8d906
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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