1-Fluoro-2-nitrobenzene → tert-Butyl (1-(2-nitrophenyl)piperidin-4-yl)carbamate

HRID 69833Notes

Reaction equation

HRID 69833 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][CH2:23][NH:22][CH2:21][CH2:20]1)=[O:17])([CH3:14])[CH3:13]>CCO>[N+:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[N:22]1[CH2:21][CH2:20][CH:19]([NH:18][C:16](=[O:17])[O:15][C:12]([CH3:13])([CH3:11])[CH3:14])[CH2:24][CH2:23]1)([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 738951-Fluoro-2-nitrobenzeneHCID 7238334-(N-Boc-amino)piperidine

Product 1

HCID 53255688tert-Butyl (1-(2-nitrophenyl)piperidin-4-yl)carbamateYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The method of Example 1 was followed using 1-fluoro-2-nitrobenzene (1.0 eq), 4-N-Boc-aminopiperidine (1.2 eq), and TEA (2.0 eq) in EtOH at 55° C. for 48 hours yielding tert-butyl 1-(2-nitro phenyl)piperidin-4-ylcarbamate (100%). LCMS (m/z): 322.2 (MH+); LC Rt=3.15 min.

Workup

  1. customat 55° C.
  2. customfor 48 hours

Sources & evidence

ORD record
ord-19c6d757750c4c0cae9e914b2216f12e
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Reaction notes

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