Hexane → HCID 23153457, compound

HRID 492754Notes

Reaction equation

HRID 492754 reaction equation
[N+:1]([C:4]1[CH:30]=[CH:29][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[CH2:28][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[CH2:28][CH2:27][CH2:26][CH2:25]4)[CH2:22][CH2:23]3)=[O:17])[CH:10]=2)=[CH:29][CH:30]=1

Participants

8

Reactant 3

HCID 8058HexaneHCID 866021634-(Pyrrolidin-1-yl)piperidine-1-carboxylic acid [4-(4-nitrophenoxy)pyridin-2-yl]amideHCID 178418361HCID 178418361, compound

Product 1

HCID 23153457HCID 23153457, compoundYield 54.9%

Reagents, catalysts & solvents 4

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

Procedure

4-(Pyrrolidin-1-yl)piperidine-1-carboxylic acid [4-(4-nitrophenoxy)pyridin-2-yl]amide (117 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 and dried under aeration to provide the titled compound (59.5 mg, 54.7%).

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
  7. customdried under aeration

Sources & evidence

ORD record
ord-4909cd0d57ac4cd0a1206683622484f5
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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