Triethylamine → 1-[3-(4-Cyano-phenyl)propyl]-6-phenylsulphonamido-1,2,3,4-tetrahydro-quinoline

HRID 379684Notes

Reaction equation

HRID 379684 reaction equation
[C:1]1([S:7]([NH:10][C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[NH:17][CH2:16][CH2:15][CH2:14]3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:28]([C:30]1[CH:35]=[CH:34][C:33]([CH2:36][CH2:37][CH2:38]I)=[CH:32][CH:31]=1)#[N:29]>CN(C)C=O>[C:28]([C:30]1[CH:35]=[CH:34][C:33]([CH2:36][CH2:37][CH2:38][N:17]2[C:18]3[C:13](=[CH:12][C:11]([NH:10][S:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)(=[O:9])=[O:8])=[CH:20][CH:19]=3)[CH2:14][CH2:15][CH2:16]2)=[CH:32][CH:31]=1)#[N:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 110335346-Phenylsulphonamido-1,2,3,4-tetrahydro-quinolineHCID 223906924-(3-Iodopropyl)benzonitrile

Product 1

HCID 183671701-[3-(4-Cyano-phenyl)propyl]-6-phenylsulphonamido-1,2,3,4-tetrahydro-quinoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
45 °C

Procedure

1.73 g 6-phenylsulphonamido-1,2,3,4-tetrahydro-quinoline are dissolved with 0.7 g triethylamine in 10 ml of dimethylformamide and combined with 1.62 g of 3-(4-cyanophenyl)propyliodide in 15 ml of dimethylformamide and stirred for 5 hours at 40-50° C. Then the mixture is evaporated down, the residue is dissolved in ethyl acetate/water, the organic phase is dried and concentrated by evaporation in vacuo. The product is chromatographed with methylene chloride/ethyl acetate (19:1) over a silica gel column.

Workup

  1. customThen the mixture is evaporated down
  2. dissolutionthe residue is dissolved in ethyl acetate/water
  3. customthe organic phase is dried
  4. concentrationconcentrated by evaporation in vacuo
  5. customThe product is chromatographed with methylene chloride/ethyl acetate (19:1) over a silica gel column

Sources & evidence

ORD record
ord-8312ad3697134ee280c992e73f503488
Source dataset
uspto-grants-2001_10
Patent number
US06300342B1

Reaction notes

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