Benzylamine → HCID 18767798, compound

HRID 2300223Notes

Reaction equation

[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([N:15]2[CH2:19][CH2:18][CH:17](OS(C)(=O)=O)[CH2:16]2)(=[O:14])=[O:13])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].[CH2:25]([NH2:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>O1CCCC1>[CH2:25]([NH:32][CH:17]1[CH2:18][CH2:19][N:15]([S:12]([C:9]2[CH:10]=[CH:11][C:6]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])=[CH:7][CH:8]=2)(=[O:14])=[O:13])[CH2:16]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of methanesulfonic acid 1-(4-butoxy-benzenesulfonyl)-pyrrolidin-3-yl ester (1.51 g, 4 mmol) in tetrahydrofuran (8 ml) was added benzylamine (3.46 g, 32 mmol) and the mixture was stirred at 100° C. for 2 days. After cooling to room temperature the tetrahydrofuran was evaporated, and the residue washed with hexanes. The solid was stirred with 10% sodium carbonate solution (30 ml) and ethyl acetate (40 ml), and the organic solution was washed brine, dried over anhydrous sodium sulfate, and filtered through Magnolsol. The filtrate was evaporated, and the residue was washed with hexanes to give 1.49 g of a white solid; m.p. 99-100° C.; MS (ES) m/z 389.0 (MH+); HRMS (El) Calcd. for C21H28N2O3S (M+): 388.1820, Found: 388.1826.

Workup

customwas evaporated
washthe residue washed with hexanes
stirringThe solid was stirred with 10% sodium carbonate solution (30 ml) and ethyl acetate (40 ml)
washthe organic solution was washed brine
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered through Magnolsol
customThe filtrate was evaporated
washthe residue was washed with hexanes

Sources & evidence

ORD record: ord-f0a10b9f8d4b408898a7f514e120164b
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06498170B2

Reaction notes

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