Hydrochloric Acid → HCID 18917249, compound

HRID 5590Notes

Reaction equation

HRID 5590 reaction equation
C1(C)C=CC(S(O[CH2:11][CH2:12][CH:13]2[C:19]3[CH:20]=[C:21]([Cl:24])[CH:22]=[CH:23][C:18]=3[N:17]([C:25](=[O:43])[C:26]3[CH:31]=[CH:30][C:29]([NH:32][C:33](=[O:41])[C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=4[CH3:40])=[CH:28][C:27]=3[CH3:42])[CH2:16][CH2:15][CH2:14]2)(=O)=O)=CC=1.[I-].[Na+].[C:47]([N:50]1[CH2:55][CH2:54][NH:53][CH2:52][CH2:51]1)(=[O:49])[CH3:48].Cl>CN(C)C=O.C(OCC)C>[ClH:24].[C:47]([N:50]1[CH2:55][CH2:54][N:53]([CH2:11][CH2:12][CH:13]2[C:19]3[CH:20]=[C:21]([Cl:24])[CH:22]=[CH:23][C:18]=3[N:17]([C:25](=[O:43])[C:26]3[CH:31]=[CH:30][C:29]([NH:32][C:33](=[O:41])[C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=4[CH3:40])=[CH:28][C:27]=3[CH3:42])[CH2:16][CH2:15][CH2:14]2)[CH2:52][CH2:51]1)(=[O:49])[CH3:48]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 837951-AcetylpiperazineHCID 189174665-[2-(p-toluenesulfonyloxy)ethyl]-7-chloro-1-[2-methyl-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine

Product 1

HCID 18917249HCID 18917249, compoundYield 121.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-[2-(p-toluenesulfonyloxy)ethyl]-7-chloro-1-[2-methyl-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.25 g) in dry dimethylformamide (20 ml) are added sodium iodide (0.178 g) and 4-acetylpiperazine (0.152 g), and the mixture is stirred at room temperature for one hour. The mixture is heated at 50° C. for 2 hours, and further at 60° C. for 3 hours. To the reaction solution are added 1N-hydrochloric acid and diethyl ether, and the aqueous layer is collected and neutralized with saturated aqueous sodium hydrogen carbonate solution, and extracted with dichloromethane. The dichloromethane layer is washed with water, dried, and the solvent is distilled off. To the resulting residue is added hydrochloric acid/ethanol to give 5-[2-(4-acetyl-1-piperazinyl)ethyl]-7-chloro-1-[2-methyl-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine hydrochloride (150 mg) as colorless amorphous.

Workup

  1. temperatureThe mixture is heated at 50° C. for 2 hours
  2. waitfurther at 60° C. for 3 hours
  3. customthe aqueous layer is collected
  4. extractionextracted with dichloromethane
  5. washThe dichloromethane layer is washed with water
  6. customdried
  7. distillationthe solvent is distilled off
  8. additionTo the resulting residue is added hydrochloric acid/ethanol

Sources & evidence

ORD record
ord-51fadc04c6db458b83e946b701fe0f2a
Source dataset
uspto-grants-1993_09
Patent number
US05244898

Reaction notes

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