Monomethylamine methanol → (4-aminomethylbenzyl)-(4-dipropylaminobutyl)carbamic Acid t-butyl Ester

HRID 348612Notes

Reaction equation

HRID 348612 reaction equation
[C:1]([O:5][C:6](=[O:38])[N:7]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][N:27]2C(=O)C3C(=CC=CC=3)C2=O)=[CH:22][CH:21]=1)[CH2:8][CH2:9][CH2:10][CH2:11][N:12]([CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15])([CH3:4])([CH3:3])[CH3:2].CN.CO>>[C:1]([O:5][C:6](=[O:38])[N:7]([CH2:19][C:20]1[CH:21]=[CH:22][C:23]([CH2:26][NH2:27])=[CH:24][CH:25]=1)[CH2:8][CH2:9][CH2:10][CH2:11][N:12]([CH2:13][CH2:14][CH3:15])[CH2:16][CH2:17][CH3:18])([CH3:3])([CH3:4])[CH3:2]

Participants

3

Reactant 2

HCID 57454252Monomethylamine methanolHCID 66941390[4-(1,3-Dioxo-1,3-dihydroisoindol-2-ylmethyl)benzyl]-(4-dipropylaminobutyl) carbamic acid t-butyl ester

Product 1

HCID 66941409(4-aminomethylbenzyl)-(4-dipropylaminobutyl)carbamic Acid t-butyl EsterYield 124.7%

Procedure

The compound (70.0 mg) obtained in Example 25-3 was added with a 40% methylamine/methanol solution (3.0 ml) and then stirred at room temperature for 14 hours. After completion of the reaction, the solvent was distilled off. Then, the residue was then added with a 1 mol/l sodium hydroxide aqueous solution and chloroform to extract the aqueous layer therefrom with chloroform. The extract was dried with anhydrous sodium sulfate, and the solvent was distilled off, thereby obtaining the subject compound (65.5 mg) as a colorless viscous liquid.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off
  3. additionThen, the residue was then added with a 1 mol/l sodium hydroxide aqueous solution and chloroform
  4. extractionto extract the aqueous layer
  5. dry with materialThe extract was dried with anhydrous sodium sulfate
  6. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-70b24bd92935481a80503cfb1bd49d36
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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