1,4-Dioxane hydrochloride → 2-[(4-Aminomethyl-benzyl)-(4-dipropylamino-butyl)-amino]-malonic acid diethyl ester

HRID 2080883Notes

Reaction equation

HRID 2080883 reaction equation
[CH2:1]([O:3][C:4](=[O:39])[CH:5]([N:11]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][NH:31]C(OC(C)(C)C)=O)=[CH:26][CH:25]=1)[CH2:12][CH2:13][CH2:14][CH2:15][N:16]([CH2:20][CH2:21][CH3:22])[CH2:17][CH2:18][CH3:19])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].Cl.O1CCOCC1>C(O)C>[CH2:9]([O:8][C:6](=[O:7])[CH:5]([N:11]([CH2:23][C:24]1[CH:25]=[CH:26][C:27]([CH2:30][NH2:31])=[CH:28][CH:29]=1)[CH2:12][CH2:13][CH2:14][CH2:15][N:16]([CH2:17][CH2:18][CH3:19])[CH2:20][CH2:21][CH3:22])[C:4]([O:3][CH2:1][CH3:2])=[O:39])[CH3:10]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 671038582-[[4-(t-Butoxycarbonylamino-methyl)-benzyl]-(4-dipropylamino-butyl)-amino]-malonic acid diethyl ester

Product 1

HCID 671033212-[(4-Aminomethyl-benzyl)-(4-dipropylamino-butyl)-amino]-malonic acid diethyl esterYield 98.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The compound (421 mg) obtained in Example 89-1 was dissolved in anhydrous ethanol (4.0 ml) and added with a 4 mol/l hydrogen chloride/dioxane solution (4.00 ml) and the whole was stirred at room temperature for 3 hours. After completion of the reaction, the solvent was distilled off. The resultant was added with a 1 mol/l sodium hydroxide aqueous solution and the whole was subjected to extraction with chloroform and washed with a saturated saline solution. The organic layer was dried with anhydrous sodium sulfate. The solvent was distilled off, thereby obtaining the subject compound (338 mg) as a pale-yellow oily substance.

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. extractionthe whole was subjected to extraction with chloroform
  5. washwashed 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-00a7e068e0654020bc7ef4d92c7ca8d3
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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