1-Fluoro-2-nitrobenzene → Tert-butyl 1-(2-nitrophenyl)piperidin-3-ylcarbamate

HRID 69832

Reaction equation

HRID 69832 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[CH3:11][C:12]([O:15][C:16]([NH:18][CH:19]1[CH2:24][NH:23][CH2:22][CH2:21][CH2:20]1)=[O:17])([CH3:14])[CH3:13].CCN(C(C)C)C(C)C>CCO>[N+:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[N:23]1[CH2:22][CH2:21][CH2:20][CH:19]([NH:18][C:16](=[O:17])[O:15][C:12]([CH3:13])([CH3:11])[CH3:14])[CH2:24]1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 738951-Fluoro-2-nitrobenzeneHCID 81531DiisopropylethylamineHCID 42330413-(Boc-amino)piperidine

Product 1

HCID 68162429Tert-butyl 1-(2-nitrophenyl)piperidin-3-ylcarbamateYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The method of Example 1 was followed using 1-fluoro-2-nitrobenzene (1.0 eq), 3-N-Boc-aminopiperidine (1.0 eq), and DIEA (2.0 eq) in EtOH at 50° C. for 48 hours yielding tert-butyl 1-(2-nitrophenyl)piperidin-3-ylcarbamate (85%). LCMS (m/z): 322.2 (MH+); LC Rt=3.23 min.

Workup

  1. customat 50° C.
  2. customfor 48 hours

Sources & evidence

ORD record
ord-d70960dc09ae40e8bb85428a1a0e5f1b
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Linked notes

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