6-Methyl-1,2,3,4-tetrahydroquinoline → 2,4,6-Trimethyl-N-[2,2,2-trifluoro-1-(6-methyl-3,4-dihydro-2H-quinolin-1-ylmethyl)ethyl]benzenesulfonamide

HRID 1868428Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH2:7][CH2:6][CH2:5]2.[F:12][C:13]([F:30])([F:29])[CH:14]1[CH2:16][N:15]1[S:17]([C:20]1[C:25]([CH3:26])=[CH:24][C:23]([CH3:27])=[CH:22][C:21]=1[CH3:28])(=[O:19])=[O:18]>C1COCC1>[CH3:28][C:21]1[CH:22]=[C:23]([CH3:27])[CH:24]=[C:25]([CH3:26])[C:20]=1[S:17]([NH:15][CH:14]([CH2:16][N:8]1[C:9]2[C:4](=[CH:3][C:2]([CH3:1])=[CH:11][CH:10]=2)[CH2:5][CH2:6][CH2:7]1)[C:13]([F:30])([F:12])[F:29])(=[O:18])=[O:19]

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 46 mg (0.31 mmol) of 6-methyl-1,2,3,4-tetrahydroquinoline and 91.5 mg (0.31 mmol) of 2-trifluoromethyl-1-(2,4,6-trimethylbenzenesulfonyl)aziridine in 1.5 mL of anhydrous THF was heated at 130° C. in a sealed tube for 18 hours. The mixture was concentrated and the residue was purified by silica gel chromatography eluting with ethyl acetate-hexanes (gradient) to afford 65 mg (47%), m.p. 143° C.-144° C.

Workup

concentrationThe mixture was concentrated
customthe residue was purified by silica gel chromatography
washeluting with ethyl acetate-hexanes (gradient)
customto afford 65 mg (47%), m.p. 143° C.-144° C.

Sources & evidence

ORD record: ord-309a4410aa8c4028b0fa9434ba338686
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07635711B2

Reaction notes

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