2-Iodophenol → 4-(2-Iodophenoxymethyl)-1-methyl-1,2,3,6-tetrahydropyridine

HRID 1741030Notes

Reaction equation

HRID 1741030 reaction equation
[OH:1][CH2:2][C:3]1[CH2:4][CH2:5][N:6]([CH3:9])[CH2:7][CH:8]=1.[I:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[I:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:1][CH2:2][C:3]1[CH2:8][CH2:7][N:6]([CH3:9])[CH2:5][CH:4]=1

Participants

6

Reactant 4

HCID 107842-IodophenolHCID 11776TriphenylphosphineHCID 1189211,2,3,6-Tetrahydro-1-methylpyridine-4-methanolHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 107350934-(2-Iodophenoxymethyl)-1-methyl-1,2,3,6-tetrahydropyridineYield 66.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(Hydroxymethyl)-1-methyl-1,2,3,6-tetrahydropyridine (D1, 5.63 g, 0.044 mol), 2-iodophenol (7.80 g, 0.035 mol) and triphenylphosphine (11.61 g, 0.044 mol) were stirred in dry THF (200 ml) under Ar as diethyl azodicarboxylate (7.0 ml, 0.044 mol) was added portionwise. The solution was stirred for 1 h, concentrated, diluted with ethyl acetate, and extracted with dil. HCl. The extract was basified (sat. K2CO3 solution) and extracted with ethyl acetate. This organic extract was dried (Na2SO4) and evaporated to give a brown oil. Purification by chromatography on silica gel, eluting with 0-10% methanol/chloroform (gradient) gave the title compound (7.65 g, 65%) as an amber oil.

Workup

  1. additionwas added portionwise
  2. concentrationconcentrated
  3. additiondiluted with ethyl acetate
  4. extractionextracted with dil. HCl
  5. extractionextracted with ethyl acetate
  6. extractionThis organic extract
  7. dry with materialwas dried (Na2SO4)
  8. customevaporated
  9. customto give a brown oil
  10. customPurification by chromatography on silica gel
  11. washeluting with 0-10% methanol/chloroform (gradient)

Sources & evidence

ORD record
ord-ec64b1cbb0c74ae58332e6548c22bf09
Source dataset
uspto-grants-1999_10
Patent number
US05972951

Reaction notes

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