Benzonitrile, 4-chloro-3-nitro- → Tert-butyl 1-(4-cyano-2-nitrophenyl)piperidin-3-ylcarbamate

HRID 69858

Reaction equation

HRID 69858 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[C:13]([NH:20][CH:21]1[CH2:26][CH2:25][CH2:24][NH:23][CH2:22]1)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].CCN(C(C)C)C(C)C>>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([N:23]2[CH2:24][CH2:25][CH2:26][CH:21]([NH:20][C:13](=[O:14])[O:15][C:16]([CH3:18])([CH3:17])[CH3:19])[CH2:22]2)=[C:3]([N+:10]([O-:12])=[O:11])[CH:4]=1)#[N:7]

Participants

4

Reactant 3

HCID 13655Benzonitrile, 4-chloro-3-nitro-HCID 81531DiisopropylethylamineHCID 42330413-(Boc-amino)piperidine

Product 1

HCID 69044928Tert-butyl 1-(4-cyano-2-nitrophenyl)piperidin-3-ylcarbamateYield 95%

Procedure

Method 1 was followed using 4-chloro-3-nitrobenzonitrile (1.0 eq), 3-(N-Boc-amino) piperidine (1.0 eq), and DIEA (2.4 eq) at 55° C. for 24 hours yielding tert-butyl 1-(4-cyano-2-nitrophenyl)piperidin-3-ylcarbamate (95%). LCMS (m/z): 347.2 (MH+); LC Rt=3.06 min.

Workup

  1. customat 55° C.
  2. customfor 24 hours

Sources & evidence

ORD record
ord-860ccf97d2074f9eb5a0742f83cd25f7
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Linked notes

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