Water → HCID 135855963, compound

HRID 395478Notes

Reaction equation

HRID 395478 reaction equation
[CH3:1][N:2]([CH:22]1[CH2:27][CH2:26][N:25]([CH2:28][C:29]2[CH:34]=[CH:33][N:32]=[C:31]([C:35]3[CH:40]=[C:39]([O:41][CH3:42])[C:38]([O:43]C)=[C:37]([O:45][CH3:46])[CH:36]=3)[CH:30]=2)[CH2:24][CH2:23]1)[CH2:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:10]2[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18]C)=[C:12]([O:20][CH3:21])[CH:11]=2)[CH:5]=1.I[Si](C)(C)C.O.C(=O)([O-])O.[Na+].[Cl:58]CCl>C(OCC)(=O)C>[ClH:58].[ClH:58].[ClH:58].[ClH:58].[CH3:1][N:2]([CH:22]1[CH2:23][CH2:24][N:25]([CH2:28][C:29]2[CH:34]=[CH:33][N:32]=[C:31]([C:35]3[CH:36]=[C:37]([O:45][CH3:46])[C:38]([OH:43])=[C:39]([O:41][CH3:42])[CH:40]=3)[CH:30]=2)[CH2:26][CH2:27]1)[CH2:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:10]2[CH:11]=[C:12]([O:20][CH3:21])[C:13]([OH:18])=[C:14]([O:16][CH3:17])[CH:15]=2)[CH:5]=1

Participants

7

Reactant 5

HCID 962WaterHCID 6344DichloromethaneHCID 85247Trimethylsilyl iodideHCID 516892Sodium BicarbonateHCID 10416543HCID 10416543, compound

Product 1

HCID 135855963HCID 135855963, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To an ice-cooled solution of 4-[N-methyl-N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]amino]-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidine (100 mg) in dichloromethane (5 mL) was added iodotrimethylsilane (173 μL). The mixture was stirred at 0° C. for 2 hours and then at room temperature overnight. A small amount of water, ethyl acetate and saturated aqueous sodium hydrogencarbonate were added to the mixture at 0° C. and the organic layer was separated. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and evaporated. The residue was applied to a preparative TLC using chloroform-ammonia saturated methanol (15:1) to give a free base of the title compound which was converted to a tetrahydrochloride by the conventional method.

Workup

  1. customat room temperature
  2. customovernight
  3. customthe organic layer was separated
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-51efeb5e68114d66a5bb16beca1792e6
Source dataset
uspto-grants-2003_08
Patent number
US06605620B1

Reaction notes

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