Morpholine → 6-(Morpholin-4-yl)pyridin-2-amine

HRID 1504762Notes

Reaction equation

HRID 1504762 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][CH:3]=1.[NH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1>[Cl-].[NH4+].C(Cl)Cl>[N:9]1([C:2]2[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][CH:3]=2)[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1

Participants

5

Reactant 2

HCID 8083MorpholineHCID 2062462-Amino-6-chloropyridine

Product 1

HCID 187718606-(Morpholin-4-yl)pyridin-2-amine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
200 °C

Procedure

6-Chloropyridin-2-amine (244 mg, 1.90 mmol) and morpholine (0.827 mL, 9.49 mmol) were combined and heated for 2 hr at 200° C. via microwave irradiation. The reaction mixture was diluted with saturated aqueous ammonium chloride and DCM. The organics were separated, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (10-80% acetone/hexanes, linear gradient) to afford 6-(morpholin-4-yl)pyridin-2-amine. MS ESI calc'd. for C9H14N3O [M+H]+ 180. found 180. 1H NMR (500 MHz, CDCl3) δ 7.29 (t, J=7.9 Hz, 1H), 5.99 (d, J=8.1 Hz, 1H), 5.91 (d, J=7.8 Hz, 1H), 3.82-3.75 (m, 4H), 3.46-3.38 (m, 4H).

Workup

  1. customThe organics were separated
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel chromatography (10-80% acetone/hexanes, linear gradient)

Sources & evidence

ORD record
ord-f2efc2b2736d4c7ba34858ce17e8400f
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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