4-Hydroxybenzaldehyde → HCID 86760174, compound

HRID 1792748Notes

Reaction equation

HRID 1792748 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[Cl:10][C:11]1[N:16]=[N:15][C:14]([N:17]2[CH2:22][CH2:21][CH:20](CCO)[CH2:19][CH2:18]2)=[CH:13][CH:12]=1.[CH2:26](O)[CH3:27]>O>[Cl:10][C:11]1[N:16]=[N:15][C:14]([N:17]2[CH2:18][CH2:19][CH2:20][CH2:21][CH:22]2[CH2:26][CH2:27][O:1][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 702EthanolHCID 149892211-(6-Chloro-3-pyridazinyl)-4-piperidineethanol

Product 1

HCID 86760174HCID 86760174, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4- {2-[1-(6-Chloro-3-pyridazinyl)piperidinyl]ethoxy}benzaldehyde (Intermediate IIa) was prepared from 4-hydroxybenzaldehyde and 2-[1-(6-Chloro-3-pyridazinyl)-4-piperidinyl]ethanol using a Mitsunobu Reaction and following the general methods described in U.S. Pat. No. 4,992,433. The aldehyde (60 mg, 0.17 mmol) was dissolved in ethanol (5 ml) with stirring at room temperature and a solution of ethoxyanine in water (0.5 ml, 50% EtONH2) was added. The reaction was stirred at room temperature for 2 days and then concentrated on a rotary evaporator and the residue was purified by chromatography (silica gel 18g) using chloroform as eluent. The first compound to elute was the O-ethyloxime (1) which was obtained as a pale cream solid (30mg, 44%).

Workup

  1. customa Mitsunobu Reaction
  2. stirringThe reaction was stirred at room temperature for 2 days
  3. concentrationconcentrated on a rotary evaporator
  4. customthe residue was purified by chromatography (silica gel 18g)
  5. washThe first compound to elute

Sources & evidence

ORD record
ord-787609c5fc094e55af8b9d71496b9fb7
Source dataset
uspto-grants-2006_07
Patent number
US07078403B1

Reaction notes

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