Water → HCID 12291568, compound

HRID 1637743Notes

Reaction equation

HRID 1637743 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][C:5]([CH2:8]Cl)=[CH:4][CH:3]=1.[NH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1.O>C(Cl)Cl>[N:10]1([CH2:8][C:5]2[CH:6]=[CH:7][N:2]=[CH:3][CH:4]=2)[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 962WaterHCID 8083MorpholineHCID 745704-(Chloromethyl)pyridinium chloride

Product 1

HCID 12291568HCID 12291568, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 4-picolyl chloride hydrochloride (10.0 g, 60.98 mmol) in 100 ml of methylene chloride at room temperature is treated with morpholine (26.52 g, 304.9 mmol, 5.0 equiv.) at once. After stirring for 50 h, the reaction mixture is poured into 250 ml of water, extracted six times with ethylacetate, three times with ethylacetate-methanol (9:1) and the combined organic extracts are dried over Na2SO4. The concentrated filtrate is chromatographed with 350 g of silica gel, packed and eluted with acetone-methylene chloride (1:2), to give 9.17 g (84%) of 4-(4-morpholinyl)methylpyridine as a yellow liquid.

Workup

  1. extractionextracted six times with ethylacetate, three times with ethylacetate-methanol (9:1)
  2. dry with materialthe combined organic extracts are dried over Na2SO4
  3. customThe concentrated filtrate is chromatographed with 350 g of silica gel
  4. washeluted with acetone-methylene chloride (1:2)

Sources & evidence

ORD record
ord-95f5d281d4cc4aafbe0100df9d5b592e
Source dataset
uspto-grants-2000_03
Patent number
US06043248

Reaction notes

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