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

HRID 2080863Notes

Reaction equation

HRID 2080863 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 76-2 was added with a 40% methylamine/methanol solution (3.0 ml) and the whole was stirred at room temperature for 14 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 chloroform to extract the aqueous layer with chloroform. The resultant 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. additionThe resultant was added with a 1 mol/l sodium hydroxide aqueous solution and chloroform
  4. extractionto extract the aqueous layer with chloroform
  5. dry with materialThe resultant was dried with anhydrous sodium sulfate
  6. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-32c07dad60dc41fcb19fa3f6592deac6
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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