Diltiazem → cis-3-(Acetyloxy)-2,3,4,5-tetrahydro-2-(4-methoxyphenyl)-N-[2-(3,5-dimethoxyphenyl)ethyl]-N,N-dimethyl-4-oxo-1,5-benzothiazepine-5-ethanaminium iodide

HRID 568784Notes

Reaction equation

[CH3:1][C:2]([O:4][C@H:5]1[C:15](=[O:16])[N:14]([CH2:17][CH2:18][N:19]([CH3:21])[CH3:20])[C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[S:7][C@H:6]1[C:22]1[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=1)=[O:3].[CH3:30][O:31][C:32]1[CH:33]=[C:34]([CH:38]=[C:39]([O:41][CH3:42])[CH:40]=1)[CH2:35][CH2:36][I:37]>CCOC(C)=O>[I-:37].[C:2]([O:4][C@H:5]1[C:15](=[O:16])[N:14]([CH2:17][CH2:18][N+:19]([CH2:36][CH2:35][C:34]2[CH:38]=[C:39]([O:41][CH3:42])[CH:40]=[C:32]([O:31][CH3:30])[CH:33]=2)([CH3:21])[CH3:20])[C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[S:7][C@H:6]1[C:22]1[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=1)(=[O:3])[CH3:1]

Participants

Conditions

Temperature: 50 °C

Procedure

To a flask under nitrogen was added 5.0 g (0.0121 mole) of diltiazem, 3.52 g (0.0121 mole) of 3,5-dimethoxyphenethyl iodide, and 20 ml of EtOAc. The reaction mixture was heated at 50° C. for 24 hr then at 75° C. for 97 hr. The reaction was cooled to RT, the solvent decanted, and the oily residue washed three times with EtOAc. The oily residue was dissolved in methylene chloride, washed with water and dried over MgSO4. The solvent was evaporated to give 5.45 g of a mixture of the title product and diltiazem hydroiodide as a tan foam.

Workup

temperatureThe reaction was cooled to RT
customthe solvent decanted
washthe oily residue washed three times with EtOAc
dissolutionThe oily residue was dissolved in methylene chloride
washwashed with water
dry with materialdried over MgSO4
customThe solvent was evaporated

Sources & evidence

ORD record: ord-5867a41daf9544d99acdef383e874dc3
Source dataset: uspto-grants-1988_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04729994

Reaction notes

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