Hydrochloric Acid → HCID 11384068, compound

HRID 221205Notes

Reaction equation

HRID 221205 reaction equation
[CH2:1]([N:4]1[CH2:10][CH2:9][C:8]2[CH:11]=[CH:12][C:13]([NH2:15])=[CH:14][C:7]=2[CH2:6][CH2:5]1)[CH2:2][CH3:3].[C:16]([NH:19][C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1)(=[O:18])[CH3:17].C(N(CC)CC)C.Cl.[OH-].[Na+]>O1CCCC1>[CH2:1]([N:4]1[CH2:10][CH2:9][C:8]2[CH:11]=[CH:12][C:13]([NH:15][S:26]([C:23]3[CH:22]=[CH:21][C:20]([NH:19][C:16](=[O:18])[CH3:17])=[CH:25][CH:24]=3)(=[O:28])=[O:27])=[CH:14][C:7]=2[CH2:6][CH2:5]1)[CH2:2][CH3:3]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 8481N-Acetylsulfanilyl chlorideHCID 14798Sodium HydroxideHCID 67226850HCID 67226850, compound

Product 1

HCID 11384068HCID 11384068, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

400 mg (1.96 mmol) of 3-propyl-2,3,4,5-tetrahydro-1H-3-benzazepine-7-amine and 1.86 mmol of 4-acetylaminobenzenesulfonyl chloride were dissolved in 20 ml of tetrahydrofuran at room temperature, 0.82 ml (5.87 mmol) of triethylamine was added dropwise, and the mixture was stirred at room temperature overnight. After the solvent had been evaporated off, 20 ml of water were added, and the mixture was acidified with 1 mol of hydrochloric acid and extracted with 50 ml of diethyl ether. The aqueous phase was made basic at pH 9-10 with 1 mol of sodium hydroxide solution and then extracted with diethyl ether. The residue obtained after drying with sodium sulfate and after removal of the solvent was converted into the hydrochloride with ethereal hydrochloric acid. Yield: 280 mg (35% of theory)

Workup

  1. customAfter the solvent had been evaporated off
  2. addition20 ml of water were added
  3. extractionextracted with 50 ml of diethyl ether
  4. extractionextracted with diethyl ether
  5. customThe residue obtained
  6. dry with materialafter drying with sodium sulfate
  7. customafter removal of the solvent

Sources & evidence

ORD record
ord-4fd67dc3ed6c4cbdad42f861a8e5fbda
Source dataset
uspto-grants-2012_06
Patent number
US08207160B2

Reaction notes

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