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

HRID 1173927Notes

Reaction equation

HRID 1173927 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 77-1 was dissolved in methanol (10 ml) and then added with a 4 mol/l hydrogen chloride/dioxane solution (15 ml), followed by stirring at room temperature for 30 minutes. The reaction solution was concentrated under reduced pressure and added with anion-exchange resin (Amberlite IRA-410) in methanol to adjust the solution to pH 8. After the resin had been removed through filtration, the solvent was distilled off, thereby obtaining the subject compound (0.79 g) as a yellow solid.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionadded with anion-exchange resin (Amberlite IRA-410) in methanol
  3. customAfter the resin had been removed through filtration
  4. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-f94f790996514d1fab10f0ae06e8e312
Source dataset
uspto-grants-2010_11
Patent number
US07833991B2

Reaction notes

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