4-Fluoro-3-nitrotoluene → Tert-butyl 1-(4-methyl-2-nitrophenyl)piperidin-3-ylcarbamate

HRID 69852

Reaction equation

HRID 69852 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[C:12]([NH:19][CH:20]1[CH2:25][CH2:24][CH2:23][NH:22][CH2:21]1)([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13]>>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([N:22]2[CH2:23][CH2:24][CH2:25][CH:20]([NH:19][C:12](=[O:13])[O:14][C:15]([CH3:17])([CH3:16])[CH3:18])[CH2:21]2)=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1

Participants

3

Reactant 2

HCID 1362874-Fluoro-3-nitrotolueneHCID 42330413-(Boc-amino)piperidine

Product 1

HCID 69042669Tert-butyl 1-(4-methyl-2-nitrophenyl)piperidin-3-ylcarbamateYield 87%

Procedure

Method 1 was followed using 4-fluoro-3-nitrotoluene (1.0 eq), 3-(N-Boc-amino) piperidine (1.2 eq), and TEA (1.5 eq) at 55° C. for 48 hours yielding tert-butyl 1-(4-methyl-2-nitrophenyl)piperidin-3-ylcarbamate (87%). LCMS (m/z): 336.1 (MH+); LC Rt=3.41 min.

Workup

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

Sources & evidence

ORD record
ord-d6542b82100a4505976c0ca61186557c
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Linked notes

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