3-[3-(1,3-Dioxolan-2-yl)phenoxy]propanamine → 1-Amino-2-{3-[3-(1,3-dioxolan-2-yl)phenoxy]propylamino}-1-cyclobutene-3,4-dione

HRID 1651344Notes

Reaction equation

HRID 1651344 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:7]=[C:8]([CH:14]=[CH:15][CH:16]=1)[O:9][CH2:10][CH2:11][CH2:12][NH2:13].[NH2:17][C:18]1[C:21](=[O:22])[C:20](=[O:23])[C:19]=1OCCCC>CO>[NH2:17][C:18]1[C:21](=[O:22])[C:20](=[O:23])[C:19]=1[NH:13][CH2:12][CH2:11][CH2:10][O:9][C:8]1[CH:14]=[CH:15][CH:16]=[C:6]([CH:2]2[O:3][CH2:4][CH2:5][O:1]2)[CH:7]=1

Participants

4

Reactant 2

HCID 127974473-[3-(1,3-Dioxolan-2-yl)phenoxy]propanamineHCID 145450343-Amino-4-n-butoxy-3-cyclobutene-1,2-dione

Product 1

HCID 230519051-Amino-2-{3-[3-(1,3-dioxolan-2-yl)phenoxy]propylamino}-1-cyclobutene-3,4-dioneYield 99.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-[3-(1,3-dioxolan-2-yl)phenoxy]propylamine (12.62 g, 56.5 mmole) and 1-amino-2-butoxy-1-cyclobutene-3,4-dione (10.0 g, 56.5 mmole) in 250 mL of methanol was stirred at ambient temperature. After 21 hours, the thick reaction mixture was filtered and the filter cake was washed with cold methanol. The collected solid was dried in vacuo to give 17.9 g of the title compound.

Workup

  1. filtrationthe thick reaction mixture was filtered
  2. washthe filter cake was washed with cold methanol
  3. customThe collected solid was dried in vacuo

Sources & evidence

ORD record
ord-510db829af9e4127bf72c582cc773eb4
Source dataset
uspto-grants-1990_05
Patent number
US04927968

Reaction notes

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