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

HRID 2059917Notes

Reaction equation

HRID 2059917 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[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>C1COCC1>[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 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a slurry of LAH (656 mg, 17.3 mmol, 3.0 eq) in THF (50 ml) was added dropwise diethyl 2,2′-(1-benzylpiperidine-4,4-diyl)diacetate (2 g, 5.76 mmol) in THF (10 ml) at 0° C. The reaction mixture was stirred at room temperature overnight. The reaction was quenched with THF/water (0.7 ml water in 7 ml THF). Then the mixture was stirred for 1 h at room temperature, filtered through celite and concentrated to dryness to yield the desired compound. The crude product was used directly in next step without further purification. Yield: 80%

Workup

  1. customThe reaction was quenched with THF/water (0.7 ml water in 7 ml THF)
  2. stirringThen the mixture was stirred for 1 h at room temperature
  3. filtrationfiltered through celite and
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-8b600462fa9c4649bf2cec8122eb4d28
Source dataset
uspto-grants-2012_10
Patent number
US08278319B2

Reaction notes

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