Triethylamine → 2-Isopropyl-5-(4-methanesulfonyl-piperazin-1-yl)-4-methoxy-phenol

HRID 81837Notes

Reaction equation

[CH:1]([C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[CH:6][C:5]=1[OH:18])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>ClCCl>[CH:1]([C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([N:12]2[CH2:13][CH2:14][N:15]([S:27]([CH3:26])(=[O:29])=[O:28])[CH2:16][CH2:17]2)=[CH:6][C:5]=1[OH:18])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirring solution of 2-Isopropyl-4-methoxy-5-piperazin-1-yl-phenol (0.47 g, 1.88 mmol) in dichloromethane at 0° C. under nitrogen was added triethylamine (0.26 mL, 1.89 mmol), followed by methanesulfonyl chloride (0.15 mL, 1.89 mmol). The reaction mixture was stirred at 0° C. for five minutes, and then allowed to warm to room temperature. The reaction mixture was partitioned between dichloromethane and water, and the organic layer was separated, washed with water, dried (MgSO4), filtered, and evaporated under reduced pressure. The residue was purified via flash chromatography (hexanes:EtOAc 3:2) to afford 0.1 g (16%) of 2-Isopropyl-5-(4-methanesulfonyl-piperazin-1-yl)-4-methoxy-phenol as an oil.

Workup

temperatureto warm to room temperature
customThe reaction mixture was partitioned between dichloromethane and water
customthe organic layer was separated
washwashed with water
dry with materialdried (MgSO4)
filtrationfiltered
customevaporated under reduced pressure
customThe residue was purified via flash chromatography (hexanes:EtOAc 3:2)

Sources & evidence

ORD record: ord-4383bf394c16406590fdbae627d81dd2
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846705B2

Reaction notes

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