2-Chloro-3-nitropyridine → 1-Benzyl-4-[N-cyclopentyl-N-(3-nitro-2-pyridinyl)amino]piperidine

HRID 361818Notes

Reaction equation

HRID 361818 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][CH3:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][CH:20]=[CH:19][N:18]=1.Br[C:27]1[C:32](OCC)=[CH:31][CH:30]=[CH:29]N=1>>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH:29]2[CH2:30][CH2:31][CH2:32][CH2:27]2)[C:15]2[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][CH:20]=[CH:19][N:18]=2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 796132-Chloro-3-nitropyridineHCID 41361281-benzyl-N-methylpiperidin-4-amineHCID 106319262-Bromo-3-ethoxypyridine

Product 1

HCID 544381711-Benzyl-4-[N-cyclopentyl-N-(3-nitro-2-pyridinyl)amino]piperidine

Procedure

Following the general procedure of EXAMPLE 70, and making non-critical variations but substituting 1-benzyl-4-(1-cyclopentylamino)piperidine (EXAMPLE 103) for 1-benzyl-4-(methylamino)piperidine and 2-chloro-3-nitropyridine for 2-bromo-3-ethoxypyridine and using a reaction time of 2 hrs, the title compound is obtained, NMR (CDCl3) 8.26, 7.91, 7.33-7.21, 6.67, 3.78, 3.47, 2.97-2.86, 2.11, 1.98-1.75 and 1.50δ.

Workup

  1. customa reaction time of 2 hrs

Sources & evidence

ORD record
ord-f2a371a9602c419a97b7fe36d6ce2380
Source dataset
uspto-grants-1999_02
Patent number
US05866589

Reaction notes

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