Hydrochloric Acid → HCID 67769616, compound

HRID 1440280Notes

Reaction equation

HRID 1440280 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12](=[O:29])[C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:28])[C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[Cl:27])=[N:15][CH:14]=3)[CH:10](C=C=O)[CH2:9][CH2:8][CH:7]([N:33]3[CH2:38][CH2:37][N:36](C(OC(C)(C)C)=O)[CH2:35][CH2:34]3)[C:6]=2[CH:46]=1.Cl.[OH2:48].[OH-].[Na+].[O:51]1[CH2:56][CH2:55]OCC1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12](=[O:29])[C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:28])[C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[Cl:27])=[N:15][CH:14]=3)[CH:10]([CH2:55][C:56]([OH:51])=[O:48])[CH2:9][CH2:8][CH:7]([N:33]3[CH2:34][CH2:35][NH:36][CH2:37][CH2:38]3)[C:6]=2[CH:46]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 86749345HCID 86749345, compound

Product 1

HCID 67769616HCID 67769616, compound

Procedure

To a solution of 7-chloro-5-(4-t-butoxycarbonyl-1-piperazinyl)-carbonylmethyl-1-[6-(2-chlorobenzoylamino)nicotinoyl]-2,3,4,5-tetrahydro-1H-benzazepine (1.2 g)in dioxane (20 ml)is added 5 N hydrochloric acid (2 ml), and the mixture is stirred at room temperature overnight. Water is added to the reaction mixture, and the mixture is made basic with aqueous sodium hydroxide solution, and extracted with dichloromethane. The extract is washed with water, dried over magnesium sulfate, and evaporated under reduced pressure to remove the solvent. The residue is purified by silica gel column chromatography, and recrystallized from ethyl acetate-diethyl ether to give 7-chloro-5-(1-piperazinyl)carboxymethyl-1-[6-(2-chlorobenzoylamino)nicotinoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.54 g) as white powder.

Workup

  1. extractionextracted with dichloromethane
  2. washThe extract is washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customto remove the solvent
  6. customThe residue is purified by silica gel column chromatography
  7. customrecrystallized from ethyl acetate-diethyl ether

Sources & evidence

ORD record
ord-f746ea66658e41e8a3cd4d39c19e3730
Source dataset
uspto-grants-1996_03
Patent number
US05498609

Reaction notes

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