Hydrochloric Acid → 2-[6-(4-Methoxyphenyl)pyridin-3-yl]propan-2-amine benzenesulfonate

HRID 386603Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[CH:13][C:12]([C:15]([NH:18]C(=O)C)([CH3:17])[CH3:16])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.Cl.[OH-].[Na+].[C:25]1([S:31]([OH:34])(=[O:33])=[O:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O>[C:25]1([S:31]([OH:34])(=[O:33])=[O:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:14]=[CH:13][C:12]([C:15]([NH2:18])([CH3:16])[CH3:17])=[CH:11][CH:10]=2)=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 100 °C

Procedure

The product of Step C, 1-C, (23.34 g, 82 mmol) was suspended in H2O (66 mL) and cone. HCl (58.1 mL, 708 mmol). The reaction mixture was heated at 100° C. for 24 h. The reaction mixture was cooled to rt and partitioned with MTBE. The organic layer was discarded. The aqueous layer was treated with aq. 5.0 M NaOH (160 mL, 800 mmol) and extracted with EtOAc (2×˜700 mL). The combined organic layers were dried (MgSO4), filtered and concentrated under reduced pressure to about ¼ of the original volume. Benzenesulfonic acid (12.98 g, 82 mmol) was added as a solid and the mixture was agitated and allowed to stand at rt for 10 min. The solids were isolated by vacuum filtration, rinsed with hexanes and dried under high vacuum. HPLC/MS: 243.0 (M+1); Rt=1.49 min.

Workup

temperatureThe reaction mixture was cooled to rt
custompartitioned with MTBE
extractionextracted with EtOAc (2×˜700 mL)
dry with materialThe combined organic layers were dried (MgSO4)
filtrationfiltered
concentrationconcentrated under reduced pressure to about ¼ of the original volume
customThe solids were isolated by vacuum filtration
washrinsed with hexanes
customdried under high vacuum

Sources & evidence

ORD record: ord-fb345d3874924a478f696af505ba506e
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372857B2

Reaction notes

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