Hydrochloric Acid → 5-((4-Bromo-2-formylphenyl)(4-methoxybenzyl)amino)pentanoic acid

HRID 402268Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6]([CH2:7][N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]2=[O:14])=[CH:5][CH:4]=1.[OH-].[Na+].Cl.C(=O)([O-])[O-:21].[Na+].[Na+].[Br:26][C:27]1[CH:28]=[CH:29][C:30](F)=[C:31]([CH:34]=1)[CH:32]=[O:33]>CS(C)=O>[Br:26][C:27]1[CH:28]=[CH:29][C:30]([N:8]([CH2:7][C:6]2[CH:15]=[CH:16][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH2:13][CH2:12][CH2:11][CH2:10][C:9]([OH:21])=[O:14])=[C:31]([CH:32]=[O:33])[CH:34]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To 1-(4-methoxybenzyl)piperidin-2-one (50.0 g) was added aqueous 4N sodium hydroxide solution (228 ml) and then the mixture was refluxed for a day. The mixture was cooled to 0° C. and concentrated hydrochloric acid (76 ml) was added thereto. The mixture was neutralized. Then, after adding sodium carbonate (53.8 g) and dimethyl sulfoxide (600 ml), 5-bromo-2-fluorobenzaldehyde (38.6 g) was added dropwise at 135° C. to the mixture. After refluxing for 5 hours, the mixture was neutralized with 3N hydrochloric acid at 0° C., and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, after which it was dried with magnesium sulfate. The solvent was distilled off under reduced pressure to give 5-((4-bromo-2-formylphenyl)(4-methoxybenzyl)amino)pentanoic acid (77.2 g) as a brown oily material.

Workup

temperaturethe mixture was refluxed for a day
additionwas added dropwise at 135° C. to the mixture
temperatureAfter refluxing for 5 hours
extractionextracted with ethyl acetate
washThe organic layer was washed with water and saturated brine
dry with materialafter which it was dried with magnesium sulfate
distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record: ord-3fe3d86cb0404120a56ed88219c1cb6a
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08741943B2

Reaction notes

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