3-(3-Aminopropoxy)-N,N-dimethylbenzenemethanamine → HCID 67947014, compound

HRID 2296030Notes

Reaction equation

HRID 2296030 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:6]=[C:7]([CH:13]=[CH:14][CH:15]=1)[O:8][CH2:9][CH2:10][CH2:11][NH2:12])[CH3:3].C1([NH:24][C:25](SC)=[CH:26][N+:27]([O-:29])=[O:28])CCCCCCC1>C(#N)C>[CH3:1][N:2]([CH2:4][C:5]1[CH:6]=[C:7]([CH:13]=[CH:14][CH:15]=1)[O:8][CH2:9][CH2:10][CH2:11][NH:12][C:25]([NH2:24])=[CH:26][N+:27]([O-:29])=[O:28])[CH3:3]

Participants

4

Reactant 2

HCID 129139503-(3-Aminopropoxy)-N,N-dimethylbenzenemethanamineHCID 24155283HCID 24155283, compound

Product 1

HCID 67947014HCID 67947014, compoundYield 35.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 3-[3-[(dimethylamino)methyl]phenoxy]-propylamine (0.28 g) and 1-cyclooctylamino-1-methylthio-2-nitroethene (0.36 g) in acetonitrile (5 ml) was heated at 80° for 10 days. The solvent was then evaporated in vacuo and the residue partitioned between water (15 ml) and chloroform (15 ml). The aqueous phase was then extracted with chloroform (2×25 ml) and the combined organic extracts were washed with brine (50 ml), dried (Na2SO4) and evaporated in vacuo. The residue was purified by column chromatography on alumina using pentane/chloroform mixtures as eluant to give N-[3-[3-[(dimethylamino)methyl]phenoxy]propyl]-2-nitro-1,1-ethenediamine (0.14 g) as an orange oil.

Workup

  1. customThe solvent was then evaporated in vacuo
  2. customthe residue partitioned between water (15 ml) and chloroform (15 ml)
  3. extractionThe aqueous phase was then extracted with chloroform (2×25 ml)
  4. washthe combined organic extracts were washed with brine (50 ml)
  5. dry with materialdried (Na2SO4)
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography on alumina

Sources & evidence

ORD record
ord-8c9d16730c724c7582f336a155ce4464
Source dataset
uspto-grants-1984_01
Patent number
US04427685

Reaction notes

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