Acetic Acid → Methyl 3-[3-[[2-(4-chlorophenyl)-4-methylthiazol-5-yl]methylamino]piperidin-1-yl]benzoate

HRID 602162Notes

Reaction equation

HRID 602162 reaction equation
C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH2:19][CH:20]1[CH2:25][CH2:24][CH2:23][N:22]([C:26]2[CH:27]=[C:28]([CH:33]=[CH:34][CH:35]=2)[C:29]([O:31][CH3:32])=[O:30])[CH2:21]1.[Cl:36][C:37]1[CH:42]=[CH:41][C:40]([C:43]2[S:44][C:45]([CH:49]=O)=[C:46]([CH3:48])[N:47]=2)=[CH:39][CH:38]=1.C(=O)(O)[O-].[Na+]>O1CCCC1>[Cl:36][C:37]1[CH:38]=[CH:39][C:40]([C:43]2[S:44][C:45]([CH2:49][NH:19][CH:20]3[CH2:25][CH2:24][CH2:23][N:22]([C:26]4[CH:27]=[C:28]([CH:33]=[CH:34][CH:35]=4)[C:29]([O:31][CH3:32])=[O:30])[CH2:21]3)=[C:46]([CH3:48])[N:47]=2)=[CH:41][CH:42]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 123440802-(4-Chlorophenyl)-4-methyl-1,3-thiazole-5-carbaldehydeHCID 58992611Methyl 3-(3-aminopiperidin-1-yl)benzoate

Product 1

HCID 58992682Methyl 3-[3-[[2-(4-chlorophenyl)-4-methylthiazol-5-yl]methylamino]piperidin-1-yl]benzoateYield 39%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Acetic acid (0.0251 mL, 0.438 mmol) and sodium triacetoxyborohydride (97.7 mg, 0.438 mmol) were added to methyl 3-(3-aminopiperidin-1-yl)benzoate (79.0 mg, 0.337 mmol) and 2-(4-chlorophenyl)-4-methylthiazole-5-carboaldehyde (80.1 mg, 0.337 mmol) in tetrahydrofuran (5 mL). The reaction mixture was stirred at room temperature for 16 hours. Subsequently, a saturated aqueous sodium bicarbonate solution was added to make the mixture basic. The mixture was then 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 Sylysia Chemical Co., Ltd.) hexane:ethyl acetate=5:1->2:1) gave 59.4 mg (39%) of the desired compound as a colorless oil.

Workup

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

Sources & evidence

ORD record
ord-b8994125cbbe4c9b9e85b2c8ae2fe569
Source dataset
uspto-grants-2011_03
Patent number
US07902367B2

Reaction notes

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