Hydrogen Bromide → (+/-)-cis-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(N-methyl-N-n-propylamino)ethyl]-8-chloro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one hydrobromide

HRID 1285350Notes

Reaction equation

HRID 1285350 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[C@@H:15]([OH:16])[C:14](=[O:17])[NH:13][C:12]3[CH:18]=[CH:19][C:20]([Cl:22])=[CH:21][C:11]=3[S:10]2)=[CH:5][CH:4]=1.Cl.[CH3:24][N:25]([CH2:29][CH2:30]Cl)[CH2:26][CH2:27][CH3:28].[BrH:32]>>[BrH:32].[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[C@@H:15]([OH:16])[C:14](=[O:17])[N:13]([CH2:30][CH2:29][N:25]([CH3:24])[CH2:26][CH2:27][CH3:28])[C:12]3[CH:18]=[CH:19][C:20]([Cl:22])=[CH:21][C:11]=3[S:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 30312081-Propanamine, N-(2-chloroethyl)-N-methyl-, hydrochlorideHCID 15593400HCID 15593400, compound

Product 1

HCID 86740628(+/-)-cis-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(N-methyl-N-n-propylamino)ethyl]-8-chloro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one hydrobromide

Procedure

2 g of (±)-cis-2-(4-methoxyphenyl)-3-hydroxy-8-chloro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one and 1.13 g of 2-(N-methyl-N-n-propylamino)ethyl chloride hydrochloride are treated in the same manner as described in Example 5. The product is converted to its hydrobromide and recrystallized from a mixture of ethanol and ether. 2.1 g of (±)-cis-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(N-methyl-N-n-propylamino)ethyl]-8-chloro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one hydrobromide are thereby obtained as colorless prisms.

Workup

  1. customrecrystallized from a mixture of ethanol and ether

Sources & evidence

ORD record
ord-5718645c1354457c9a70cbc5290795f9
Source dataset
uspto-grants-1986_01
Patent number
US04567175

Reaction notes

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