Diisobutylaluminum hydride → N-(1-(4-(hydroxymethyl)phenyl)piperidin-4-yl)benzamide

HRID 591620Notes

Reaction equation

HRID 591620 reaction equation
[C:1]([NH:9][CH:10]1[CH2:15][CH2:14][N:13]([C:16]2[CH:26]=[CH:25][C:19]([C:20](OCC)=[O:21])=[CH:18][CH:17]=2)[CH2:12][CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C[AlH]CC(C)C)C>C1COCC1>[OH:21][CH2:20][C:19]1[CH:18]=[CH:17][C:16]([N:13]2[CH2:12][CH2:11][CH:10]([NH:9][C:1](=[O:8])[C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:15][CH2:14]2)=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 66670912Ethyl 4-(4-benzamidopiperidin-1-yl)benzoate

Product 1

HCID 66745757N-(1-(4-(hydroxymethyl)phenyl)piperidin-4-yl)benzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 4-(4-benzamidopiperidin-1-yl)benzoate (4.2 g, 11.9 mmol) in THF (400 mL) was cooled to 0° C. under nitrogen and treated with DIBAL-H (1.0 M in THF, 47 mL, 47 mmol). The mixture was warmed to room temperature and stirred for 1 hour. Then, the reaction mixture was quenched with Rochelle's salt (10% aqueous), concentrated to remove the THF, brine (300 mL) was added, and the organic phase was extracted with CH2Cl2 (3×200 mL), dried over anhydrous MgSO4, filtered, and concentrated, to afford N-(1-(4-(hydroxymethyl)phenyl)piperidin-4-yl)benzamide as a yellow solid that was used without further purification.

Workup

  1. customThen, the reaction mixture was quenched with Rochelle's salt (10% aqueous)
  2. concentrationconcentrated
  3. customto remove the THF, brine (300 mL)
  4. additionwas added
  5. extractionthe organic phase was extracted with CH2Cl2 (3×200 mL)
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-82448bb50de94a589e8dc9c42f65ce2f
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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