[2-Dimethylamino-6-methoxybenzothien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanone → [2-(3,4-Dimethoxyphenyl)-6-methoxybenzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanone

HRID 609813Notes

Reaction equation

HRID 609813 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].[CH3:32][O:33][C:34]1[CH:35]=[C:36]([Mg]Br)[CH:37]=[CH:38][C:39]=1[O:40][CH3:41]>C1COCC1>[CH3:32][O:33][C:34]1[CH:35]=[C:36]([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[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]3)=[CH:12][CH:11]=2)=[O:9])[CH:37]=[CH:38][C:39]=1[O:40][CH3:41]

Participants

4

Reactant 2

HCID 9954835[2-Dimethylamino-6-methoxybenzothien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanoneHCID 178491916HCID 178491916, compound

Product 1

HCID 15429200[2-(3,4-Dimethoxyphenyl)-6-methoxybenzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanoneYield 66.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

By the method described in Example 1, [2-dimethylamino-6-methoxybenzothien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]-methanone (1.64 g, 3.75 mmol) in THF (15 mL) was treated with a 0.63 M solution of 3,4-dimethoxyphenylmagnesium bromide (12.0 mL, 7.56 mmol) (prepared from 4-bromoveratrole, catalytic iodine, and magnesium turnings in THF). Purification by chromatography (silica gel, 5-10% MeOH in CH2Cl2) gave 1.32 g (66%) of the title compound as a yellow foam: 1H NMR d 1.45 (m, 2H), 1.61 (m, 4H), 2.48 (m, 4H), 2.75 (t, J=6.0 Hz, 2H), 3.74 (s, 3H), 3.84 (s, 3H), 3.90 (s, 3H), 4.09 (t, J=6.0 Hz, 2H), 6.76 (d, J=8.2 Hz, 1H), 6.77 (d, J=8.7 Hz, 2H), 6.91 (d, J=1.6 Hz, 1H), 6.98 (dd, J=2.2 Hz, 8.9 Hz, 1H), 7.04 (dd, J=1.6 Hz, 8.2 Hz, 1H), 7.33 (d, J=2.2 Hz, 1H), 7.57 (d, J=8.9 Hz, 1H), 7.79 (d, J=8.7 Hz, 2H); 13C NMR d 23.6, 25.3, 54.5, 55.1, 55.2, 55.3, 57.1, 65.6, 104.0, 110.6, 111.6, 113.7, 114.3, 121.0, 123.5, 125.7, 129.9, 130.1, 131.7, 133.4, 139.5, 141.8, 148.1, 148.7, 157.2, 162.5, 192.8; MS (FD) m/e 531 (M+); Anal. calc'd. for C31H33NO5S: C, 70.03; H, 6.26; N, 2.63. Found: C, 70.21; H, 6.36; N, 2.67.

Workup

  1. customPurification by chromatography (silica gel, 5-10% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-6dad74f581f840c3861a24759849430e
Source dataset
uspto-grants-1999_12
Patent number
US05998442

Reaction notes

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