diethyl 2,2'-(1-benzylpiperidine-4,4-diyl)diacetate → 2,2'-(1-Benzylpiperidine-4,4-diyl)di(ethan-1-ol)

HRID 2223936Notes

Reaction equation

HRID 2223936 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[CH2:19][CH2:18][C:17]([CH2:26][C:27](OCC)=[O:28])([CH2:20][C:21](OCC)=[O:22])[CH2:16][CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>O1CCCC1>[CH2:7]([N:14]1[CH2:19][CH2:18][C:17]([CH2:20][CH2:21][OH:22])([CH2:26][CH2:27][OH:28])[CH2:16][CH2:15]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 272009diethyl 2,2'-(1-benzylpiperidine-4,4-diyl)diacetateHCID 21226445Aluminium lithium hydride

Product 1

HCID 152958272,2'-(1-Benzylpiperidine-4,4-diyl)di(ethan-1-ol)Yield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To an ice-cooled solution of lithium aluminum hydride (0.76 g) in tetrahydrofuran (120 mL) was added a solution of diethyl 1-benzylpiperidine-4,4-diacetate (3.47 g) in tetrahydrofuran (10 mL) dropwise. The ice bath was removed and the reaction solution was stirred at room temperature for 1 hour. The reaction solution was again ice-cooled, to which water (0.76 mL), a 15% aqueous sodium hydroxide solution (0.76 mL) and water (2.28 mL) were added successively. The substance thus separated out was filtered off with Celite. The filtrate was concentrated under reduced pressure to give the title compound (ca. 2.63 g). This product was subjected to the subsequent step without further purification.

Workup

  1. customThe ice bath was removed
  2. temperaturecooled, to which water (0.76 mL)
  3. additiona 15% aqueous sodium hydroxide solution (0.76 mL) and water (2.28 mL) were added successively
  4. customThe substance thus separated out
  5. filtrationwas filtered off with Celite
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6dd275a85f4b422488f7c9e6d8e099d3
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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