Sodium Bicarbonate → Methyl 2-[3-[[2-(4-chlorophenyl)-4-methylthiazol-5-yl]methoxymethyl]piperidin-1-yl]benzoate

HRID 602141Notes

Reaction equation

HRID 602141 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([CH2:14][O:15][CH2:16][CH:17]3[CH2:22][CH2:21][CH2:20][N:19]([C:23]4[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=4[CH:25]=[O:26])[CH2:18]3)=[C:11]([CH3:13])[N:12]=2)=[CH:4][CH:3]=1.[Na].[C:32](=O)(O)[O-:33].[Na+]>CO.[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:9][C:10]([CH2:14][O:15][CH2:16][CH:17]3[CH2:22][CH2:21][CH2:20][N:19]([C:23]4[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=4[C:25]([O:33][CH3:32])=[O:26])[CH2:18]3)=[C:11]([CH3:13])[N:12]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 575722032-[3-[[2-(4-Chlorophenyl)-4-methylthiazol-5-yl]methoxymethyl]piperidin-1-yl]benzaldehyde

Product 1

HCID 58992617Methyl 2-[3-[[2-(4-chlorophenyl)-4-methylthiazol-5-yl]methoxymethyl]piperidin-1-yl]benzoateYield 58%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 887MethanolSolvent

Procedure

2-[3-[[2-(4-Chlorophenyl)-4-methylthiazol-5-yl]methoxymethyl]piperidin-1-yl]benzaldehyde (45.2 mg, 0.102 mmol) was dissolved in methanol (5 mL). To this solution, sodium cyamide (25.8 mg, 0.510 mmol) and manganese dioxide (88.7 mg, 1.02 mmol) were added and the mixture was stirred at room temperature for 3 hours. Subsequently, a saturated aqueous sodium bicarbonate solution was added and the mixture was filtered through Celite. The filtrate was extracted with ethyl acetate and the extract washed with brine, followed by drying over magnesium sulfate and evaporation of the solvent. Purification of the resulting residue by silica gel column chromatography (Chromatorex NH-DM2035, Fuji Silysia Chemical Co., Ltd.) (hexane:ethyl acetate=50:1->10:1) gave 27.9 mg (58%) of the desired compound as a colorless oil.

Workup

  1. filtrationthe mixture was filtered through Celite
  2. extractionThe filtrate was extracted with ethyl acetate
  3. washthe extract washed with brine
  4. dry with materialby drying over magnesium sulfate and evaporation of the solvent
  5. customPurification of the resulting residue by silica gel column chromatography (Chromatorex NH-DM2035, Fuji Silysia Chemical Co., Ltd.) (hexane:ethyl acetate=50:1->10:1)

Sources & evidence

ORD record
ord-6fe77a2daf7843288a06f238463ce96b
Source dataset
uspto-grants-2011_03
Patent number
US07902367B2

Reaction notes

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