Dimethylamine → HCID 9984330, compound

HRID 1082139Notes

Reaction equation

HRID 1082139 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10](/[C:13](/[C:23]2[CH:28]=[CH:27][C:26]([I:29])=[CH:25][CH:24]=2)=[C:14](\[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)/[CH2:15][CH3:16])=[CH:9][CH:8]=1.[CH3:30][NH:31][CH3:32].CCOCC>CO>[CH3:30][N:31]([CH3:32])[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10](/[C:13](/[C:23]2[CH:28]=[CH:27][C:26]([I:29])=[CH:25][CH:24]=2)=[C:14](\[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)/[CH2:15][CH3:16])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 3283Diethyl EtherHCID 10459222HCID 10459222, compound

Product 1

HCID 9984330HCID 9984330, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of E-1-(4-(4-chlorobutoxy)phenyl)-1-(4-iodophenyl)-2-phenyl-1-butene (0.429 g, 0.83 mmol) and dimethylamine in methanol solution (30 ml, 30%) was heated In a sealed bomb at 100° C. for 2 h, then poured into ether (75 ml), and washed with brine (100 ml) and water (2×100 ml). The organic layer was dried (Na2SO4), and concentrated in vacuo. The residues were purified by flash chromatography (silica; eluant:0-10% methanol in ether) to give the title compound as an off white solid (0.391 g, 89%) mp 74°-77° C.

Workup

  1. washwashed with brine (100 ml) and water (2×100 ml)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customThe residues were purified by flash chromatography (silica; eluant:0-10% methanol in ether)

Sources & evidence

ORD record
ord-6ba6e80cdace4090adbd25eee30b3258
Source dataset
uspto-grants-1996_12
Patent number
US05589500

Reaction notes

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