Hexane → [2-(4-Trifluoromethylphenyl)-6-methoxybenzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanone

HRID 609822Notes

Reaction equation

HRID 609822 reaction equation
CN(C)[C:3]1[S:4][C:5]2[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:6]=2[C:7]=1[C:8]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[CH:12][CH:11]=1)=[O:9].[F:32][C:33]([F:43])([F:42])[C:34]1[CH:39]=[CH:38][C:37]([Mg]Br)=[CH:36][CH:35]=1.CCCCCC.C(OCC)(=O)C>C1COCC1.CO>[F:32][C:33]([F:43])([F:42])[C:34]1[CH:39]=[CH:38][C:37]([C:3]2[S:4][C:5]3[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:6]=3[C:7]=2[C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][N:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)=[CH:12][CH:11]=2)=[O:9])=[CH:36][CH:35]=1

Participants

7

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 9954835[2-Dimethylamino-6-methoxybenzothien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanoneHCID 178506198HCID 178506198, compound

Product 1

HCID 10673987[2-(4-Trifluoromethylphenyl)-6-methoxybenzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanoneYield 81%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

By the method described in Example 1, [2-dimethylamino-6-methoxybenzothien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]-methanone (1.0 g, 2.28 mmol) in THF (20 mL) was treated with a 0.69 M THF solution of 4-trifluoromethylphenylmagnesium bromide (10 mL, 6.9 mmol) (prepared from 4-bromobenzotrifluoride, catalytic iodine, and magnesium turnings in THF) to provide, after radial chromatography (silica gel, 4:1:.05-3:1:.05 hexane:ethyl acetate:MeOH, under an ammonia atmosphere) 991 mg (81%) of the title compound as a yellow oil: 1H NMR d 1.45 (m, 2H), 1.63 (m, 4H), 2.54 (m, 4H), 2.79 (t, J=5.8 Hz, 2H), 3.89 (s, 3H), 4.13 (t, J=5.8 Hz, 2H), 6.78 (d, J=8.8 Hz, 2H), 6.98 (dd, J=8.9, 2.3 Hz, 1H), 7.34 (d, J=2.2 Hz, 1H), 7.48 (d, J=8.4 Hz, 2H), 7.54 (d, J=8.4 Hz, 2H), 7.75 (d, J=8.8 Hz, 2H); 13C NMR d 24.0, 25.7, 55.0, 55.6, 57.6, 66.1, 104.4, 114.4, 115.3, 115.8, 124.5, 125.5 (q, J=3.0 Hz), 129.1, 130.2, 132.3, 133.2, 133.6, 137.3, 139.7, 140.6, 158.2, 163.3, 192.6; MS (FD+) m/e 539 (M+); Anal. calc'd. for C30H28F3NO3S: C, 66.77; H, 5.24; N, 2.60. Found: C, 66.78; H, 5.30; N, 2.43.

Workup

  1. customto provide

Sources & evidence

ORD record
ord-c13dc6e558424646ac203564fdd5fd3b
Source dataset
uspto-grants-1999_12
Patent number
US05998442

Reaction notes

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