1,4-Dioxane hydrochloride → [(4-Aminomethyl-benzyl)-(4-dipropylamino-butyl)-amino]-acetic acid ethyl ester

HRID 2080858Notes

Reaction equation

HRID 2080858 reaction equation
[CH2:1]([O:3][C:4](=[O:34])[CH2:5][N:6]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][NH:26]C(OC(C)(C)C)=O)=[CH:21][CH:20]=1)[CH2:7][CH2:8][CH2:9][CH2:10][N:11]([CH2:15][CH2:16][CH3:17])[CH2:12][CH2:13][CH3:14])[CH3:2].Cl.O1CCOCC1>C(O)C>[CH2:1]([O:3][C:4](=[O:34])[CH2:5][N:6]([CH2:18][C:19]1[CH:20]=[CH:21][C:22]([CH2:25][NH2:26])=[CH:23][CH:24]=1)[CH2:7][CH2:8][CH2:9][CH2:10][N:11]([CH2:12][CH2:13][CH3:14])[CH2:15][CH2:16][CH3:17])[CH3:2]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 67103729[[4-(t-Butoxycarbonylamino-methyl)-benzyl]-(4-dipropylamino-butyl)-amino]-acetic acid ethyl ester

Product 1

HCID 59850563[(4-Aminomethyl-benzyl)-(4-dipropylamino-butyl)-amino]-acetic acid ethyl esterYield 97.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The compound (21.265 g) obtained in Example 72-1 was dissolved in ethanol (100 ml) and added with a 4 mol/l hydrogen chloride/dioxane solution (140 ml) and the whole was stirred at room temperature for 1 hour. Subsequently, the solution was stirred at 40° C. 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 to make the pH thereof to 12. The solution was subjected to extraction with chloroform and dried with magnesium sulfate. The solvent was distilled off, thereby obtaining the subject compound (16.46 g) as a colorless oily substance.

Workup

  1. stirringSubsequently, the solution was stirred at 40° C. for 1 hour
  2. customAfter completion of the reaction
  3. distillationthe solvent was distilled off
  4. additionThe resultant was added with a 1 mol/l sodium hydroxide aqueous solution
  5. extractionThe solution was subjected to extraction with chloroform
  6. dry with materialdried with magnesium sulfate
  7. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-47c3fc6e4ed844338ed95155a7573b82
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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