Imidazole → HCID 19360596, compound

HRID 376981Notes

Reaction equation

HRID 376981 reaction equation
O[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:22])[C:13]([CH3:21])([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[CH3:14])=[CH:8][CH:7]=1.N1C=CN=C1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:47]I>C(Cl)Cl>[I:47][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:22])[C:13]([CH3:21])([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[CH3:14])=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 19360627HCID 19360627, compound

Product 1

HCID 19360596HCID 19360596, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

16.2 g (53 mmol) of 1-[4-(3-hydroxy-propoxy)-phenyl]-2-methyl-2-morpholin-4-yl-propan-1-one, 8.97 g (132 mmol) of imidazole and 34.5 g (132 mmol) of triphenyl phosphine are dissolved in 150 ml of methylene chloride. To the solution are added 27.0 g (106 mmol) of iodine and stirred at room temperature for 1 hour. 100 ml of methylene chlorideare added to the reaction mixture and washed with sodium sulfite aqueous solution and water, and dried over MgSO4. After methylene chloride is distilled off, the residue is purified by means of column chromatography on silica gel with ethyl acetate-hexane (1:3) as an eluent, and an oily product is obtained. The structure is confirmed by the 1H-NMR spectrum (CDCl3): δ [ppm] 1.31 (s, 6H), 2.30 (m, 2H), 2.57 (m, 4H), 3.38 (t, 2H), 3.69 (m, 4H), 4.11 (t, 2H), 6.91 (d, 2H), 8.60 (d, 2H).

Workup

  1. addition100 ml of methylene chlorideare added to the reaction mixture
  2. washwashed with sodium sulfite aqueous solution and water
  3. dry with materialdried over MgSO4
  4. distillationAfter methylene chloride is distilled off
  5. customthe residue is purified by means of column chromatography on silica gel with ethyl acetate-hexane (1:3) as an eluent
  6. customan oily product is obtained

Sources & evidence

ORD record
ord-2a6b206067344e0187d66c34db7e2743
Source dataset
uspto-grants-2000_02
Patent number
US06022906

Reaction notes

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