3-Hydroxybenzaldehyde → 3-[2-(Piperidin-1-yl)ethoxy]benzaldehyde

HRID 619162Notes

Reaction equation

HRID 619162 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].C([O-])([O-])=O.[K+].[K+].Cl.Cl[CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1>C(#N)C>[N:20]1([CH2:19][CH2:18][O:1][C:2]2[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=2)[CH:5]=[O:6])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochloride

Product 1

HCID 9763543-[2-(Piperidin-1-yl)ethoxy]benzaldehydeYield 60.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 3-hydroxybenzaldehyde (5.42 g, 44.38 mmol), K2CO3 (13.5 g) and acetonitrile was added N-(2-chloroethyl)piperidine hydrochloride (9.8 g). The reaction mixture was refluxed overnight, cooled to room temperature and filtered. The filtrate was stripped to give an oil which was partitioned between CHCl3 (350 ml) and 1M NaOH (200 ml). The organic layer was separated, washed with 1M NaOH (2×200 ml), treated with DARCO®, then MgSO4, filtered, and stripped to afford, as a dark oily liquid, 6.28 g of 3-[2-(1-piperdinyl)ethoxy]benzaldehyde.

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. filtrationfiltered
  3. customto give an oil which
  4. customwas partitioned between CHCl3 (350 ml) and 1M NaOH (200 ml)
  5. customThe organic layer was separated
  6. washwashed with 1M NaOH (2×200 ml)
  7. additiontreated with DARCO®
  8. filtrationMgSO4, filtered

Sources & evidence

ORD record
ord-a6cb3ffeaf5a44149fe9e82b16dcdeec
Source dataset
uspto-grants-1999_09
Patent number
US05958929

Reaction notes

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