Anisole → 4-Bromoacetyl-7-methoxy-2-(4-methoxyphenyl)-2,3,4,5-tetrahydro-1,4-benzothiazepine

HRID 36571Notes

Reaction equation

HRID 36571 reaction equation
[Br:1][CH2:2][C:3]([N:5]1[CH2:11][C:10]2[CH:12]=[C:13]([O:16][CH3:17])[CH:14]=[CH:15][C:9]=2[S:8][CH:7](Cl)[CH2:6]1)=[O:4].[C:19]1([O:25][CH3:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[Br:1][CH2:2][C:3]([N:5]1[CH2:11][C:10]2[CH:12]=[C:13]([O:16][CH3:17])[CH:14]=[CH:15][C:9]=2[S:8][CH:7]([C:22]2[CH:23]=[CH:24][C:19]([O:25][CH3:26])=[CH:20][CH:21]=2)[CH2:6]1)=[O:4]

Participants

3

Reactant 2

HCID 7519AnisoleHCID 152916644-Bromoacetyl-2-chloro-7-methoxy-2,3,4,5-tetrahydro-1,4-benzothiazepine

Product 1

HCID 152916654-Bromoacetyl-7-methoxy-2-(4-methoxyphenyl)-2,3,4,5-tetrahydro-1,4-benzothiazepineYield 74.3%

Procedure

The above-mentioned 4-bromoacetyl-2-chloro-7-methoxy-2,3,4,5-tetrahydro-1,4-benzothiazepine (0.19 g), anisole (0.07 g) end stannic chloride (0.17 g) were reacted in the same manner as in Experimental Example 13 to give 4-bromoacetyl-7-methoxy-2-(4-methoxyphenyl)-2,3,4,5-tetrahydro-1,4-benzothiazepine (0.17 g). This compound (0.1g), 4-benzyl piperidine (0.09 g) and potassium carbonate (0.11 g) were reacted in the same manner as in Experimental Example 6 to give 4-[1-(4-benzyl)piperidinyl]acetyl-7-methoxy-2-(4-methoxyphenyl)-2,3,4,5-tetrahydro-1,4-benzothiazepine (0.20 g).

Sources & evidence

ORD record
ord-a259f9fa12a74070bc9dfbd8763884b8
Source dataset
uspto-grants-1995_05
Patent number
US05416066

Reaction notes

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