4-Hydroxybenzaldehyde → HCID 86760174, compound

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

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%).