Sodium Iodide → HCID 69304209, compound

HRID 2249467Notes

Reaction equation

HRID 2249467 reaction equation
[CH3:1][C@H:2]1[CH2:7][NH:6][C@H:5]([CH3:8])[CH2:4][N:3]1[C@H:9]([C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([OH:29])[CH:24]=1)[C:10]1[CH:22]=[CH:21][C:13]([C:14]([N:16]([CH2:19][CH3:20])[CH2:17][CH3:18])=[O:15])=[CH:12][CH:11]=1.[I-].[Na+].C(N(CC)CC)C.Br[CH2:40][C:41]1[CH:50]=[CH:49][C:44]([C:45]([O:47][CH3:48])=[O:46])=[CH:43][CH:42]=1>C(#N)C>[CH2:17]([N:16]([CH2:19][CH3:20])[C:14]([C:13]1[CH:21]=[CH:22][C:10]([C@@H:9]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([OH:29])[CH:24]=2)[N:3]2[C@@H:2]([CH3:1])[CH2:7][N:6]([CH2:40][C:41]3[CH:50]=[CH:49][C:44]([C:45]([O:47][CH3:48])=[O:46])=[CH:43][CH:42]=3)[C@H:5]([CH3:8])[CH2:4]2)=[CH:11][CH:12]=1)=[O:15])[CH3:18]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 256687Methyl 4-(bromomethyl)benzoateHCID 66628813HCID 66628813, compound

Product 1

HCID 69304209HCID 69304209, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The 4-[(S)-((2S,5R)-2,5-dimethylpiperazin-1-yl)(3-hydroxyphenyl)methyl]-N,N-diethylbenzamide (0.51 g, 1.29 mmol) was dissolved in 10 mL of dry acetonitrile. Sodium iodide (20 mg, 0.13 mmol) was added and the reaction was stirred under nitrogen at room temperature during the addition of triethylamine (0.72 mL, 5.16 mmol), followed by methyl 4-(bromomethyl)benzoate (0.59 g, 2.58 mmol). The reaction mixture was stirred under nitrogen overnight. The solvent was removed by evaporation and the residue was partitioned between ethyl acetate and saturated sodium bicarbonate solution. The organic layer was washed with water, dried over Na2SO4/MgSO4 and concentrated under reduced pressure. The residual light yellow oil was purified by chromatography on silica gel (50% EtOAc in CH2Cl2) to give 0.45 g (0.83 mmol) of methyl 4-{(2R, 5S)-4-[(S)-(4-diethylcarbamoylphenyl)(3-hydroxyphenyl)methyl]-2,5-dimethyl-1-piperazinylmethyl}-benzoate as a white amorphous solid.

Workup

  1. customThe solvent was removed by evaporation
  2. customthe residue was partitioned between ethyl acetate and saturated sodium bicarbonate solution
  3. washThe organic layer was washed with water
  4. dry with materialdried over Na2SO4/MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residual light yellow oil was purified by chromatography on silica gel (50% EtOAc in CH2Cl2)

Sources & evidence

ORD record
ord-5b6b1097820549948cb5021276654d19
Source dataset
uspto-grants-2008_01
Patent number
US07314880B2

Reaction notes

Loading…