4-Chloro-3-nitrophenyl cyclopropyl ketone → Tert-butyl 1-(4-(cyclopropanecarbonyl)-2-nitrophenyl)piperidin-3-ylcarbamate

HRID 69863Notes

Reaction equation

HRID 69863 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]([NH:23][CH:24]1[CH2:29][CH2:28][CH2:27][NH:26][CH2:25]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[CH2:27][CH2:28][CH2:29][CH:24]([NH:23][C:16](=[O:17])[O:18][C:19]([CH3:21])([CH3:20])[CH3:22])[CH2:25]3)=[C:8]([N+:13]([O-:15])=[O:14])[CH:7]=2)=[O:5])[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 12682594-Chloro-3-nitrophenyl cyclopropyl ketoneHCID 42330413-(Boc-amino)piperidine

Product 1

HCID 69043896Tert-butyl 1-(4-(cyclopropanecarbonyl)-2-nitrophenyl)piperidin-3-ylcarbamateYield 96%

Procedure

Method 1 was followed using 4-chloro-3-nitrophenyl cyclopropyl ketone (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-(cyclopropanecarbonyl)-2-nitrophenyl)piperidin-3-ylcarbamate (96%). LCMS (m/z): 390.1 (MH+); LC Rt=3.28 min.

Workup

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

Sources & evidence

ORD record
ord-9a299b5b3ebe41029ca8be1e2e229ee6
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Reaction notes

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