1,4-Dioxane hydrochloride → 4-aminomethyl-N-(4-dipropylaminomethylphenyl)benzamide

HRID 2080757Notes

Reaction equation

HRID 2080757 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:31])[NH:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][N:24]([CH2:28][CH2:29][CH3:30])[CH2:25][CH2:26][CH3:27])=[CH:19][CH:18]=2)=[CH:11][CH:10]=1)(C)(C)C.Cl.O1CCOCC1>CO>[NH2:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][N:24]([CH2:28][CH2:29][CH3:30])[CH2:25][CH2:26][CH3:27])=[CH:19][CH:18]=2)=[O:31])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 66941656[4-(4-dipropylaminomethylphenylcarbamoyl)benzyl]carbamic Acid t-butyl Ester

Product 1

HCID 230791854-aminomethyl-N-(4-dipropylaminomethylphenyl)benzamideYield 92.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (545 mg) obtained in Example 15-3 was dissolved in anhydrous methanol (10 ml) and added with a 4 mol/l hydrogen chloride/dioxane solution (10.0 ml), and the whole was stirred at room temperature for 1 hour. After completion of the reaction, the solvent was distilled off. The resultant was added with a 1 mol/l sodium hydroxide aqueous solution and subjected to extraction with chloroform, followed by washing with a saturated saline solution. The organic layer was dried with anhydrous sodium sulfate and the solvent was distilled off, thereby obtaining the subject compound (389 mg) as a colorless crystal.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off
  3. additionThe resultant was added with a 1 mol/l sodium hydroxide aqueous solution
  4. extractionsubjected to extraction with chloroform
  5. washby washing with a saturated saline solution
  6. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  7. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-0bf92476406047f3a23a13e0b657eb61
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

Loading…