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

HRID 1597856Notes

Reaction equation

HRID 1597856 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].Cl.Cl[CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1>C(#N)C>[N:14]1([CH2:13][CH2:12][O:1][C:2]2[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=2)[CH:5]=[O:6])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 1013-HydroxybenzaldehydeHCID 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), K2 CO3 (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-3829d04ed65e4b4aad7b8268105c05cd
Source dataset
uspto-grants-1998_04
Patent number
US05736548

Reaction notes

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