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

HRID 348743Notes

Reaction equation

HRID 348743 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 74.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (1.38 g) obtained in Example 122-2 was dissolved in methanol (10 ml), added with a 4 mol/l hydrogen chloride/dioxane solution (15 ml), and stirred at room temperature for 30 minutes. The reaction solution was concentrated under reduced pressure and neutralized with an anion-exchange resin (Amberlite IRA-410). The solvent was concentrated under reduced pressure and the residue was dried under vacuum, thereby obtaining the subject compound (0.79 g) as a yellow solid.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. concentrationThe solvent was concentrated under reduced pressure
  3. customthe residue was dried under vacuum

Sources & evidence

ORD record
ord-02b339be2a9c4ba29f1e5e797a31cfb7
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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