Methanol → 1-(4-Methoxybenzyl)piperidine-4-carboxaldehyde

HRID 424617Notes

Reaction equation

HRID 424617 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[CH3:11][O:12][C:13]1[CH:29]=[CH:28][C:16]([CH2:17][N:18]2[CH2:23][CH2:22][CH:21]([C:24](OC)=[O:25])[CH2:20][CH2:19]2)=[CH:15][CH:14]=1.CO.[Cl-].[Na+]>C1(C)C=CC=CC=1>[CH3:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:17][N:18]2[CH2:23][CH2:22][CH:21]([CH:24]=[O:25])[CH2:20][CH2:19]2)=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 5234Sodium ChlorideHCID 21225700DiisobutylaluminumhydrideHCID 60704011HCID 60704011, compound

Product 1

HCID 178939301-(4-Methoxybenzyl)piperidine-4-carboxaldehyde

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A 1.5 M solution of diisobutylaluminium hydride in toluene (3.12 ml, 4.68 mmol) was added dropwise to a solution of methyl 1-(4-methoxybenzyl)piperidine-4-carboxylate (1.23 g, 4.68 mmol) in toluene (30 ml) under argon at −78° C. in the course of 30 min and the mixture was then stirred at this temperature for 30 min. Thereafter, methanol (15 ml) was added dropwise such that the internal temperature remained at −78° C., before the mixture was then slowly warmed to room temperature. Saturated sodium chloride solution (20 ml) was added to the reaction mixture and the suspension was filtered through sea sand. The organic phase was dried with sodium sulfate and concentrated i. vac. The residue was purified by flash chromatography with cyclohexane/ethyl acetate (1:3).

Workup

  1. customremained at −78° C., before the mixture
  2. filtrationthe suspension was filtered through sea sand
  3. dry with materialThe organic phase was dried with sodium sulfate
  4. concentrationconcentrated i
  5. customThe residue was purified by flash chromatography with cyclohexane/ethyl acetate (1:3)

Sources & evidence

ORD record
ord-bb27e75eb7a647f39d22d5a4043b3d73
Source dataset
uspto-grants-2012_01
Patent number
US08106055B2

Reaction notes

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