Sodium Nitrite → HCID 66862724, compound

HRID 2068751Notes

Reaction equation

HRID 2068751 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH:3]=1.[N:15]([O-:17])=[O:16].[Na+]>FC(F)(F)C(O)=O>[CH3:1][C:2]1[C:7]([N+:15]([O-:17])=[O:16])=[C:6]([CH3:8])[N:5]=[C:4]([N:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)[CH:3]=1

Participants

4

Reactant 2

HCID 23668193Sodium NitriteHCID 58507994HCID 58507994, compound

Product 1

HCID 66862724HCID 66862724, compoundYield 17.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
0 °C

Procedure

To 4-(4,6-dimethyl-pyridin-2-yl)-morpholine (9.4 g) dissolved in trifluoroacetic acid (250 mL) cooled to 0° C. was added sodium nitrite (3.54 g) over 15 minutes and the reaction mixture was then stirred 15 minutes at 0° C. The reaction mixture was concentrated in vacuo to app. 100 mL and the pH adjusted to 11 with concentrated aqueous sodium hydroxide (150 mL). Brine (200 mL) was added and the mixture was extracted with diethyl ether (4×150 mL), the organic phase was dried over magnesium sulfate and concentrated in vacuo. The crude product was subjected to flash chromatography (SiO2, heptane/ethylacetate 4:1) to furnish 2.01 g (17% yield) of the title compound as a yellow solid. GC-MS (m/z) 237 (M+); tR=7.69. 1H NMR (500 MHz, DMSO-d6): 2.28 (s, 3H), 2.39 (s, 3H), 3.60 (m, 4H), 3.67 (m, 4H), 6.72 (s, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionBrine (200 mL) was added
  3. extractionthe mixture was extracted with diethyl ether (4×150 mL)
  4. dry with materialthe organic phase was dried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6c15ecb76e36499faac6dc211364894b
Source dataset
uspto-grants-2012_10
Patent number
US08299071B2

Reaction notes

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