Pyridine → HCID 90017125, compound

HRID 591150Notes

Reaction equation

[CH2:1]([N:5]([CH2:19][CH2:20][CH2:21][CH3:22])[CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:18]=[CH:17][C:13]([C:14](Cl)=[O:15])=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH3:4].Cl.[CH3:24][NH:25][O:26][CH3:27].N1C=CC=CC=1>ClCCl>[CH2:1]([N:5]([CH2:19][CH2:20][CH2:21][CH3:22])[CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([N:25]([CH3:24])[O:26][CH3:27])=[O:15])=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 0 °C

Procedure

16.25 g of 4-(3-dibutylaminopropoxyl)benzoyl chloride (V) (0.05 mol) and 5.36 g of N,O-dimethyl hydroxylamine hydrochloride (0.055 mol, 1.1 eq) are dissolved in 100 mL of dichloromethane. The reaction mixture is cooled to 0° C. and 9.25 g of pyridine (0.11 mol, 2.2 eq) is added. The mixture is heated to room temperature and it is stirred for 1 hour. The solvent is evaporated in vacuum and 30 mL of brine and 30 mL of dichloromethane are added to the residue. After 15 min stirring the phases are separated and the organic phase is dried on sodium sulfate, the solvent is evaporated and the residue is purified by column chromatography (spheric silica; eluent: toluene:MTBE:methanol=5:4:1) to give 11.9 g of the title compound (VIc) (68%) as a brown solid.

Workup

temperatureThe mixture is heated to room temperature
customThe solvent is evaporated in vacuum and 30 mL of brine and 30 mL of dichloromethane
additionare added to the residue
stirringAfter 15 min stirring the phases
customare separated
customthe organic phase is dried on sodium sulfate
customthe solvent is evaporated
customthe residue is purified by column chromatography (spheric silica; eluent: toluene:MTBE:methanol=5:4:1)

Sources & evidence

ORD record: ord-131bbf51039240288ef19f81508c3930
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238636B2

Reaction notes

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