2,6-Lutidine → HCID 58638507, compound

HRID 646860

Reaction equation

HRID 646860 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:15]([O-:17])=[O:16])=[C:6]([N:8]2[CH2:13][CH2:12][CH:11]([CH3:14])[CH2:10][CH2:9]2)[CH:7]=1.[N:18]1([C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.N1C(C)=CC=CC=1C>>[CH2:27]([O:26][C:24]([N:18]1[CH2:23][CH2:22][N:21]([C:2]2[CH:3]=[CH:4][C:5]([N+:15]([O-:17])=[O:16])=[C:6]([N:8]3[CH2:13][CH2:12][CH:11]([CH3:14])[CH2:10][CH2:9]3)[CH:7]=2)[CH2:20][CH2:19]1)=[O:25])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

4

Reactant 3

HCID 79372,6-LutidineHCID 643495Benzyl piperazine-1-carboxylateHCID 586385011-(5-Chloro-2-nitro-phenyl)-4-methyl-piperidine

Product 1

HCID 58638507HCID 58638507, compound

Procedure

The procedure of Example 4, step (b) was followed using 400 mg (1.57 mmol) of 1-(5-chloro-2-nitro-phenyl)-4-methyl-piperidine (as prepared in the Example 12, step (a)) and 910 mg (4.71 mmol) of benzyl 1-piperazinecarboxylate (except that 549 μL (4.71 mmol) of 2,6-lutidine was also added) to afford, after chromatography on a 70-g silica SPE column with 40% EtOAc-hexane, 178 mg (45%) of unreacted 1-(5-chloro-2-nitro-phenyl)-4-methyl-piperidine and 245 mg (64% based on recovered starting material) of the title compound as a yellow resin: Mass spectrum (ESI, m/z): Calcd. for C24H30N4O4, 439.2 (M+H), found 439.2.

Workup

  1. additionwas also added)
  2. customto afford
  3. customafter chromatography on a 70-g silica SPE column with 40% EtOAc-hexane, 178 mg (45%) of unreacted 1-(5-chloro-2-nitro-phenyl)-4-methyl-piperidine and 245 mg (64% based on recovered starting material) of the title compound as a yellow resin

Sources & evidence

ORD record
ord-3709b27e3bbe4f8c8d1615dbf0792018
Source dataset
uspto-grants-2010_04
Patent number
US07705042B2

Linked notes

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