Tetrahydrofuran → HCID 68663581, compound

HRID 452661Notes

Reaction equation

HRID 452661 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:16]=[C:17]([CH:22]=[CH:23][C:24]=2[N+:25]([O-])=O)[C:18]([O:20][CH3:21])=[O:19])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCCC1>[C].[Pt].CO>[NH2:25][C:24]1[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][C:15]=1[NH:14][CH:11]1[CH2:10][CH2:9][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:13][CH2:12]1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 68664456HCID 68664456, compound

Product 1

HCID 68663581HCID 68663581, compoundYield 53.4%

Reagents, catalysts & solvents 2

HCID 178503042HCID 178503042, compoundCatalystHCID 887MethanolSolvent

Procedure

A mixture of methyl 3-[(1-benzylpiperidin-4-yl)amino]-4-nitrobenzoate (17.1 g, 46.3 mmol), 5% platinum carbon (5.13 g), tetrahydrofuran (115 mL) and methanol (115 mL) was stirred under a hydrogen atmosphere at room temperature overnight. The m reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=2/1) and recrystallized from diisopropyl ether/ethyl acetate to give the title compound (8.40 g, yield 53%) as pale-red crystals.

Workup

  1. customThe m reaction mixture
  2. filtrationwas filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=2/1)
  5. customrecrystallized from diisopropyl ether/ethyl acetate

Sources & evidence

ORD record
ord-94d379fe722546a1b61621339f8d7212
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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