Methanol → HCID 63705752, compound

HRID 871080Notes

Reaction equation

HRID 871080 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[N:3]=1.[O:12]1[CH2:17][CH2:16][CH:15]([CH2:18][NH2:19])[CH2:14][CH2:13]1.C(N(CC)CC)C.CO>O1CCCC1>[Cl:11][C:4]1[N:3]=[C:2]([NH:19][CH2:18][CH:15]2[CH2:16][CH2:17][O:12][CH2:13][CH2:14]2)[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 852392,6-Dichloro-3-nitropyridineHCID 27732104-Aminomethyltetrahydropyran

Product 1

HCID 63705752HCID 63705752, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 2,6-dichloro-3-nitropyridine (1 g, 5.18 mmol)), (tetrahydro-2H-pyran-4-yl)methanamine (1.044 g, 9.07 mmol) and triethylamine (2.167 mL, 15.55 mmol) in tetrahydrofuran (22.83 mL) was stirred at 0° C. for 30 minutes and at ambient temperature for 2 hours. Methanol was added (10 mL) followed by silica gel and the mixture was concentrated and purified by silica gel flash chromatography (Isco®, Redi-Sep® column), eluting with a gradient of 2-30% ethyl acetate/hexane to afford the title compound. MS (ESI) m/z 272 (M+H)+.

Workup

  1. concentrationthe mixture was concentrated
  2. custompurified by silica gel flash chromatography (Isco®, Redi-Sep® column)
  3. washeluting with a gradient of 2-30% ethyl acetate/hexane

Sources & evidence

ORD record
ord-a09a55a22eb64109aa1aa699255f986a
Source dataset
uspto-grants-2015_03
Patent number
US08969375B2

Reaction notes

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