p-Toluenesulfonic acid monohydrate → 1-Benzyl-4-methylpiperidin-3-OL 4-methylbenzenesulfonate

HRID 2122041Notes

Reaction equation

[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH3:14])[CH:10]([OH:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23]([OH:26])(=[O:25])=[O:24])=[CH:19][CH:18]=1>CC(C)=O>[C:17]1([CH3:27])[CH:18]=[CH:19][C:20]([S:23]([OH:26])(=[O:24])=[O:25])=[CH:21][CH:22]=1.[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH3:14])[CH:10]([OH:15])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of the product from Method C (65.32 grams/0.318 mol) dissolved in 175 mL of acetone and cooled to 0° C. was added a solution of para-toluenesulfonic acid monohydrate in 350 mL of acetone (dropwise) over 2 hours and the resulting mixture stirred at 0° C. for 1.5 hours. The precipitate was filtered and the filter cake washed with 90 mL of diisopropyl ether. The solid product was then dried in vacuo affording 58.55 grams (100%) of the title compound as a white solid. LRMS: 378.5 (M+1).

Workup

filtrationThe precipitate was filtered
washthe filter cake washed with 90 mL of diisopropyl ether
customThe solid product was then dried in vacuo

Sources & evidence

ORD record: ord-fb21ed1b41244f56a9cb7f02efe96c5b
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06696567B2

Reaction notes

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