Red-Al → HCID 22380765, compound

HRID 895653Notes

Reaction equation

HRID 895653 reaction equation
[CH2:1]([N:3]([CH2:39][CH3:40])[C:4]([C:6]1[CH:38]=[CH:37][C:9]([CH2:10][C:11]2[CH:36]=[CH:35][CH:34]=[CH:33][C:12]=2[O:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][CH:19]([N:22]3[C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=4[N:24]=[C:23]3[CH2:31][OH:32])[CH2:18][CH2:17]2)=[CH:8][CH:7]=1)=O)[CH3:2].COCCO[AlH2-]OCCOC.[Na+]>O1CCCC1.C1(C)C=CC=CC=1>[CH2:1]([N:3]([CH2:4][C:6]1[CH:7]=[CH:8][C:9]([CH2:10][C:11]2[CH:36]=[CH:35][CH:34]=[CH:33][C:12]=2[O:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][CH:19]([N:22]3[C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=4[N:24]=[C:23]3[CH2:31][OH:32])[CH2:18][CH2:17]2)=[CH:37][CH:38]=1)[CH2:39][CH3:40])[CH3:2]

Participants

5

Reactant 2

HCID 16684438Red-AlHCID 22380692HCID 22380692, compound

Product 1

HCID 22380765HCID 22380765, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

The 1-[2-[2-(4-diethylcarbamoylbenzyl)phenoxy]ethyl]-4-(2-hydroxymethyl-1H-benzimidazol-1-yl)piperidine (64 mg) obtained in Example 84 was dissolved in tetrahydrofuran (1.3 ml), added with a solution of Red-Al in toluene (65%, 0.18 ml) and stirred at room temperature for 2.5 hours. After the reaction mixture was slowly poured into ice 10 g with ice cooling to quench the reaction and the layers were separated, the aqueous layer was extracted with dichloromethane (30 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: dichloromethane:methanol:aqueous ammonia=9:1:0.1) to obtain 31 mg of the title compound. Yield: 50%.

Workup

  1. customto quench
  2. customthe reaction
  3. customthe layers were separated
  4. extractionthe aqueous layer was extracted with dichloromethane (30 ml)
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by preparative thin layer silica gel column chromatography (developing solvent: dichloromethane:methanol:aqueous ammonia=9:1:0.1)

Sources & evidence

ORD record
ord-f42b5f9f53954a7285ae531c4b3d790b
Source dataset
uspto-grants-2005_07
Patent number
US06916822B2

Reaction notes

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