Sodium Iodide → HCID 178430528, compound

HRID 353114Notes

Reaction equation

HRID 353114 reaction equation
[CH3:1][CH:2]1[C:7]([CH3:19])([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]3[N:15]=[N:16][NH:17][CH:18]=3)[CH:9]=2)[CH2:6][CH2:5][NH:4][CH2:3]1.Cl[CH2:21][CH2:22][CH:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[OH:24].[I-].[Na+].C(=O)([O-])O.[Na+]>CN(C)C=O>[OH:24][CH:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:22][CH2:21][N:4]1[CH2:5][CH2:6][C:7]([CH3:19])([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]3[N:15]=[N:16][NH:17][CH:18]=3)[CH:9]=2)[CH:2]([CH3:1])[CH2:3]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 516892Sodium Bicarbonate2×HCID 5720643-Chloro-1-phenylpropanolHCID 178430465HCID 178430465, compound

Product 1

HCID 178430528HCID 178430528, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3,4-dimethyl-4-(3-(1H-1,2,3-triazol-4-yl)phenyl)piperidine (Preparation 44, 50 mg, 0.20 mmol) in N,N-dimethylformamide (6 mL) was added commercially available 3-chloro-1-phenyl-1-propanol (33 mg, 0.21 mmol), sodium iodide (15 mg) and aqueous sodium hydrogencarbonate (25 mg, 0.29 mmol). The resultant mixture was heated to 80° C. and stirred overnight. The reaction mixture was cooled, poured onto saturated aqueous sodium hydrogencarbonate solution (100 mL) and extracted with ethyl acetate (3×20 mL). The combined extracts were dried over MgSO4, filtered and concentrated in vacuo to give an off-white gum. The crude product was purified by column chromatography on a 5 g silica Waters Sep-Pak3 eluting with dichloromethane and then dichloromethane:methanol (5:95) to give the title compound as a clear oil (19 mg, 25%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate (3×20 mL)
  3. dry with materialThe combined extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give an off-white gum
  7. customThe crude product was purified by column chromatography on a 5 g silica Waters Sep-Pak3
  8. washeluting with dichloromethane

Sources & evidence

ORD record
ord-610ae590df4a4af092b2ddc2e74af0a9
Source dataset
uspto-grants-2004_06
Patent number
US06750231B2

Reaction notes

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