Potassium Carbonate → HCID 66599681, compound

HRID 1909027Notes

Reaction equation

HRID 1909027 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH2:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][CH:3]=1.[CH3:12][N:13]([CH3:20])[CH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.C([O-])([O-])=O.[K+].[K+].CN(C=O)C.O>O>[CH3:12][N:13]([CH3:20])[CH:14]1[CH2:19][CH2:18][N:17]([C:2]2[N:7]=[C:6]([NH2:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][CH:3]=2)[CH2:16][CH2:15]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 417391N,N-Dimethylpiperidin-4-amineHCID 27240356-Chloro-3-nitropyridin-2-ylamineHCID 21962138N,N-Dimethylformamide--water (1/1)

Product 1

HCID 66599681HCID 66599681, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 6-chloro-3-nitro-pyridine-2-yl-amine (7 g, 40.6 mmol), dimethylpiperidine-4-yl-amine (5.7 g, 44.5 mmol), K2CO3 (6.39 g, 60.9 mmol) and DMF/water (4:1, 100 mL) was heated at 100° C. for 10 minutes in microwave reactor. After cooling, water was added and the resulting precipitate was collected by filtration and dried to give 6-(4-dimethylamino-piperidin-1-yl)-3-nitro-pyridin-2-yl-amine (9.48 g, 88%) as a yellow solid. 1H NMR (400 MHz, CD2Cl2) δ: 1.48 (m, 2H), 1.72 (m, 2H), 2.28 (s, 6H), 2.42 (m, 1H), 3.01 (m, 2H), 4.50 (m, 2H), 6.16 (d, J=9.54 Hz, 1H), 8.14 (d, J=9.54 Hz, 1H). HRMS: m/z 266.1628 [M+H]+.

Workup

  1. temperatureAfter cooling
  2. filtrationthe resulting precipitate was collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-df3ea26332a54e55b534c34d1a1ec8e6
Source dataset
uspto-grants-2013_12
Patent number
US08598217B2

Reaction notes

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