tert-Butyl piperazine-1-carboxylate → Tert-butyl 4-(4-(cyclopropanecarbonyl)-2-nitrophenyl)piperazine-1-carboxylate

HRID 69861Notes

Reaction equation

HRID 69861 reaction equation
[CH:1]1([C:4]([C:6]2[CH:11]=[CH:10][C:9](Cl)=[C:8]([N+:13]([O-:15])=[O:14])[CH:7]=2)=[O:5])[CH2:3][CH2:2]1.[C:16]([N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17]>>[CH:1]1([C:4]([C:6]2[CH:11]=[CH:10][C:9]([N:26]3[CH2:25][CH2:24][N:23]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:28][CH2:27]3)=[C:8]([N+:13]([O-:15])=[O:14])[CH:7]=2)=[O:5])[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 12682594-Chloro-3-nitrophenyl cyclopropyl ketone

Product 1

HCID 69041514Tert-butyl 4-(4-(cyclopropanecarbonyl)-2-nitrophenyl)piperazine-1-carboxylateYield 98%

Procedure

Method 1 was followed using 4-chloro-3-nitrophenyl cyclopropyl ketone (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-(cyclopropanecarbonyl)-2-nitrophenyl)piperazine-1-carboxylate (98%). LCMS (m/z): 376.1 (MH+); LC Rt=3.33 min.

Workup

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

Sources & evidence

ORD record
ord-79f593319ed245e1b41bf19185241344
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Reaction notes

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