Imidazole → 1-[4-(3-Iodopropylamino)phenyl]-2-dimethylamino-2-benzyl-butan-1-one

HRID 376966Notes

Reaction equation

HRID 376966 reaction equation
O[CH2:2][CH2:3][CH2:4][NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:26])[C:13]([N:23]([CH3:25])[CH3:24])([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:14][CH3:15])=[CH:8][CH:7]=1.N1C=CN=C1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:51]I>C(Cl)Cl>[I:51][CH2:2][CH2:3][CH2:4][NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:26])[C:13]([N:23]([CH3:25])[CH3:24])([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:14][CH3:15])=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 193606121-[4-(3-Hydroxypropylamino) phenyl]-2-dimethylamino-2-benzyl-butan-1-one

Product 1

HCID 193605921-[4-(3-Iodopropylamino)phenyl]-2-dimethylamino-2-benzyl-butan-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
20 °C

Procedure

14.5 g (0.041 mol) of 1-[4-(3-Hydroxypropylamino)phenyl]-2-dimethylamino-2-benzyl-butan-1-one, 6.96 g (0.1 mol) of imidazole and 26.8 g (0.1 mol) of triphenyl phosphine are dissolved in 100 ml of methylene chloride. To the solution are added 20.8 g (0.082 mol) of iodine and stirred at room temperature (about 20° C.) for 20 min. 200 ml of methylene chloride are added to the reaction mixture and washed with aqueous solution of sodium sulfite and water, and dried over MgSO4. After distilling off the methylene chloride, the residue is purified by means of column chromatography on silica gel with ethyl acetate-hexane (1:4) as an eluent, and an oily product is obtained. The structure is confirmed by the 1H-NMR spectrum (CDCl3): δ [ppm]: 0.68 (t, 3H), 1.82-1.88 (m, 1H), 2.02-2.35 (m, 3H), 2.35 (s, 6H), 3.17 (d, 1H), 3.20 (d, 1H), 3.27 (t, 2H), 3.34-3.37 (m, 2H), 4.17 (br, 1H), 6.53 (d, 2H), 7.15-7.28 (m, 5H), 8.32 (d, 2H).

Workup

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

Sources & evidence

ORD record
ord-76bb368b4826407b8ec63e2627391181
Source dataset
uspto-grants-2000_02
Patent number
US06022906

Reaction notes

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