4-Fluoro-3-nitrotoluene → Tert-butyl 4-(4-methyl-2-nitrophenyl)piperazine-1-carboxylate

HRID 69850

Reaction equation

HRID 69850 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]([N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]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[CH2:21][CH2:20][N:19]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:24][CH2:23]2)=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1

Participants

3

Reactant 2

HCID 1362874-Fluoro-3-nitrotolueneHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 69042835Tert-butyl 4-(4-methyl-2-nitrophenyl)piperazine-1-carboxylateYield 90%

Procedure

Method 1 was followed using 4-fluoro-3-nitrotoluene (1.0 eq), 1-Boc-piperazine (1.2 eq), and TEA (1.5 eq) at 55° C. for 48 hours yielding tert-butyl 4-(4-methyl-2-nitrophenyl)piperazine-1-carboxylate (90%). LCMS (m/z): 322.1 (MH+); LC Rt=3.46 min.

Workup

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

Sources & evidence

ORD record
ord-c2b6f359588845eba37b20a1ff46b855
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Linked notes

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