4-Fluoro-3-nitrobenzotrifluoride → Tert-butyl 1-(2-nitro-4-(trifluoromethyl)phenyl)piperidin-3-ylcarbamate

HRID 69853

Reaction equation

HRID 69853 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[C:15]([NH:22][CH:23]1[CH2:28][CH2:27][CH2:26][NH:25][CH2:24]1)([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16]>>[N+:12]([C:3]1[CH:4]=[C:5]([C:8]([F:11])([F:10])[F:9])[CH:6]=[CH:7][C:2]=1[N:25]1[CH2:26][CH2:27][CH2:28][CH:23]([NH:22][C:15](=[O:16])[O:17][C:18]([CH3:20])([CH3:19])[CH3:21])[CH2:24]1)([O-:14])=[O:13]

Participants

3

Reactant 2

HCID 677784-Fluoro-3-nitrobenzotrifluorideHCID 42330413-(Boc-amino)piperidine

Product 1

HCID 68463789Tert-butyl 1-(2-nitro-4-(trifluoromethyl)phenyl)piperidin-3-ylcarbamateYield 99%

Procedure

Method 1 was followed using 1-fluoro-2-nitro-4-(trifluoromethyl)benzene (1.0 eq), 3-(N-Boc-amino) piperidine (1.2 eq), and TEA (1.5 eq) at 55° C. for 1 hour yielding tert-butyl 1-(2-nitro-4-(trifluoromethyl)phenyl)piperidin-3-ylcarbamate (99%). LCMS (m/z): 390.1 (MH+); LC Rt=3.58 min.

Workup

  1. customat 55° C.
  2. customfor 1 hour

Sources & evidence

ORD record
ord-46c8703dfb0648658c8aed8d1237c75b
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Linked notes

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