3-Nitroaniline → HCID 90052079, compound

HRID 2284670Notes

Reaction equation

HRID 2284670 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][C:10](=O)[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[N+:15]([C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][CH:24]=1)[NH2:21])([O-:17])=[O:16].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(Cl)Cl.C(OCC)(=O)C.C(O)(=O)C>[N+:15]([C:18]1[CH:19]=[C:20]([NH:21][CH:10]2[CH2:11][CH2:12][CH2:13][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9]2)[CH:22]=[CH:23][CH:24]=1)([O-:17])=[O:16]

Participants

8

Reactant 4

HCID 74233-NitroanilineHCID 516892Sodium BicarbonateHCID 2756825Tert-butyl 3-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 90052079HCID 90052079, compoundYield 55.5%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-Boc-3-piperidinone (256 mg) and 3-nitroaniline (190 mg) in methylene chloride (7 mL), sodium triacetoxyborohydride (438 mg) and acetic acid (80 μL) were added at room temperature, and the mixture was stirred at the same temperature for 15 hours. To the reaction mixture, ethyl acetate and saturated aqueous sodium hydrogencarbonate were added. The organic layer was separated, washed with saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent, 100 to 50% hexane in ethyl acetate) to obtain tert-butyl 3-((3-nitrophenyl)amino)piperidine-1-carboxylate (C21, 229 mg).

Workup

  1. customThe organic layer was separated
  2. washwashed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (eluent, 100 to 50% hexane in ethyl acetate)

Sources & evidence

ORD record
ord-aa2ad9da4e3e4ce1ac429c02e5da2fe4
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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