Water → HCID 69720215, compound

HRID 895652Notes

Reaction equation

HRID 895652 reaction equation
[CH2:1]([N:3]([CH2:39][CH3:40])[C:4]([C:6]1[CH:38]=[CH:37][C:9]([C:10]([C:12]2[CH:36]=[CH:35][CH:34]=[CH:33][C:13]=2[O:14][CH2:15][CH2:16][N:17]2[CH2:22][CH2:21][CH:20]([N:23]3[C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=4[NH:25][C:24]3=[O:32])[CH2:19][CH2:18]2)=[O:11])=[CH:8][CH:7]=1)=[O:5])[CH3:2].[BH4-].[Na+].O>C(O)C>[CH2:39]([N:3]([CH2:1][CH3:2])[C:4]([C:6]1[CH:7]=[CH:8][C:9]([CH:10]([C:12]2[CH:36]=[CH:35][CH:34]=[CH:33][C:13]=2[O:14][CH2:15][CH2:16][N:17]2[CH2:18][CH2:19][CH:20]([N:23]3[C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=4[NH:25][C:24]3=[O:32])[CH2:21][CH2:22]2)[OH:11])=[CH:37][CH:38]=1)=[O:5])[CH3:40]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 22380574HCID 22380574, compound

Product 1

HCID 69720215HCID 69720215, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The 1-[2-[2-(4-diethylcarbamoylbenzoyl)phenoxy]ethyl]-4-(1,3-dihydro-2H-benzimidazol-2-on-1-yl)piperidine (39 mg) obtained in Example 23 was dissolved in ethanol (1 ml), added with sodium borohydride (1 mg) with ice cooling and stirred at room temperature for 30 minutes. The reaction mixture was added with water (5 ml) and extracted twice with ethyl acetate (5 ml). The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by preparative thin layer silica gel column chromatography (developing solvent: ethyl acetate:methanol=10:1) to obtain 27.2 mg of the title compound. Yield: 70%.

Workup

  1. extractionextracted twice with ethyl acetate (5 ml)
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by preparative thin layer silica gel column chromatography (developing solvent: ethyl acetate:methanol=10:1)

Sources & evidence

ORD record
ord-244e7dc551414e9da071bdf960f13c64
Source dataset
uspto-grants-2005_07
Patent number
US06916822B2

Reaction notes

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