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

HRID 361817Notes

Reaction equation

HRID 361817 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.BrC1C(OCC)=[CH:31][CH:30]=[CH:29]N=1>>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH:30]([CH3:31])[CH3:29])[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 107368561-Benzyl-4-[N-(1-methylethyl)-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-methylethylamino)piperidine (EXAMPLE 99) 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) 8.24, 7.90, 7.31-7.23, 6.62, 3.61, 3.49, 2.97, 2.27, 1.96, 1.77 and 1.39δ.

Workup

  1. customa reaction time of 2 hrs

Sources & evidence

ORD record
ord-e2fd34e68bf847748ad308344ac0f9c4
Source dataset
uspto-grants-1999_02
Patent number
US05866589

Reaction notes

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