Phenethylamine → trans-3-(2-indolecarboxamido)-4-oxo-2-phenyl-N-(2-phenylethyl)-2,3,4,5-tetrahydro 1,5-benzothiazepine-5-acetamide

HRID 345156Notes

Reaction equation

HRID 345156 reaction equation
N1C2C(=CC=CC=2)C=C1[C:10]([NH:12][C@@H:13]1[C:19](=[O:20])[N:18]([CH2:21][C:22]([OH:24])=O)[C:17]2[CH:25]=[CH:26][CH:27]=[CH:28][C:16]=2[S:15][C@H:14]1[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:11].[C:35]1([CH2:41][CH2:42][NH2:43])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C([N:48]([CH2:53][CH2:54][CH2:55][CH3:56])CCCC)CCC.[I-].ClC1[CH:64]=[CH:63][CH:62]=[CH:61][N+]=1C>C(Cl)(Cl)Cl.ClCCl>[NH:43]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:41]=[C:42]1[C:10]([NH:12][C@@H:13]1[C:19](=[O:20])[N:18]([CH2:21][C:22]([NH:48][CH2:53][CH2:54][C:55]2[CH:56]=[CH:64][CH:63]=[CH:62][CH:61]=2)=[O:24])[C:17]2[CH:25]=[CH:26][CH:27]=[CH:28][C:16]=2[S:15][C@H:14]1[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)=[O:11]

Participants

7

Reactant 4

HCID 1001PhenethylamineHCID 7622TributylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 14648568trans-3-(2-Indolecarboxamido)-4-oxo-2-phenyl-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetic acid

Product 1

HCID 14648571trans-3-(2-indolecarboxamido)-4-oxo-2-phenyl-N-(2-phenylethyl)-2,3,4,5-tetrahydro 1,5-benzothiazepine-5-acetamide

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

While a mixture of 2 g of trans-3-(2-indolecarboxamido)-4-oxo-2-phenyl-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetic acid, 20 ml of dichloromethane and 0.2 g of 2-phenylethylamine and tri-n-butylamine is stirred at room temperature, 1.2 g of 2-chloro-N-methylpyridinium iodide is added to the mixture. The mixture is stirred at room temperature for 18 hours. After chloroform is added to the reaction mixture, the mixture is washed with a 5% aqueous solution of hydrochloric acid, a saturated aqueous solution of sodium hydrogencarbonate and a saturated solution of sodium chloride. Thereafter, the mixture is dried, and the solvent is distilled off under reduced pressure. The obtained residue is separated and purified by silica gel column chromatography (eluent: chloroform), and recrystallized from ethanol to give 0.7 g of trans-3-(2-indolecarboxamido)-4-oxo-2-phenyl-N-(2-phenylethyl)-2,3,4,5-tetrahydro 1,5-benzothiazepine-5-acetamide 1/2hydrate, m.p. 157°-163° C.

Workup

  1. stirringThe mixture is stirred at room temperature for 18 hours
  2. washthe mixture is washed with a 5% aqueous solution of hydrochloric acid
  3. customThereafter, the mixture is dried
  4. distillationthe solvent is distilled off under reduced pressure
  5. customThe obtained residue is separated
  6. custompurified by silica gel column chromatography (eluent: chloroform)
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-39b6de57c4af4f87b267fe58e22c2217
Source dataset
uspto-grants-1991_10
Patent number
US05055464

Reaction notes

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