Isopropanol → 4-[2-(Hexahydro-1H-azepin-1-yl)ethoxy]phenyl 2-(4-Methoxyphenyl)benzo[b]thiophen-3-yl Ketone

HRID 1386990Notes

Reaction equation

HRID 1386990 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]3[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=3[CH:10]=2)=[CH:5][CH:4]=1.Cl.[N:19]1([CH2:26][CH2:27][O:28][C:29]2[CH:37]=[CH:36][C:32]([C:33](O)=[O:34])=[CH:31][CH:30]=2)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.C(O)(C)C>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]3[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=3[C:10]=2[C:33]([C:32]2[CH:31]=[CH:30][C:29]([O:28][CH2:27][CH2:26][N:19]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)=[CH:37][CH:36]=2)=[O:34])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 41373912-(4-Methoxyphenyl)benzothiopheneHCID 131748704-(2-Azepan-1-ylethoxy)benzoic acid hydrochloride

Product 1

HCID 99350984-[2-(Hexahydro-1H-azepin-1-yl)ethoxy]phenyl 2-(4-Methoxyphenyl)benzo[b]thiophen-3-yl KetoneYield 35%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

By essentially following the procedure detailed in Example 1, Part C, the title compound was prepared from 2-(4-methoxyphenyl)benzo[b]thiophene (Example 3; Part A) and 4-[2-(hexahydro-1H-azepin-1-yl)ethoxy]benzoic acid hydrochloride in 35% yield as an oil following radial chromatography (SiO2; gradient of 1-10% isopropanol in CH2Cl2).

Sources & evidence

ORD record
ord-f4ba7ff4fbd34bf0a4eb8ac83f4110e7
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

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