2,6-dichloro-N'-hydroxybenzene-1-carboximidamide → 1-({4-[3-(2,6-Dichlorophenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl}carbonyl)-1,2,3,4-tetrahydroquinoline

HRID 551793Notes

Reaction equation

HRID 551793 reaction equation
[N:1]1([C:11]([N:13]2[CH2:18][CH2:17][CH:16]([C:19](O)=[O:20])[CH2:15][CH2:14]2)=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.[Cl:63][C:64]1[CH:69]=[CH:68][CH:67]=[C:66]([Cl:70])[C:65]=1[C:71](=[N:73]O)[NH2:72]>O.CN(C)C=O>[Cl:63][C:64]1[CH:69]=[CH:68][CH:67]=[C:66]([Cl:70])[C:65]=1[C:71]1[N:73]=[C:19]([CH:16]2[CH2:17][CH2:18][N:13]([C:11]([N:1]3[C:2]4[C:7](=[CH:6][CH:5]=[CH:4][CH:3]=4)[CH2:8][CH2:9][CH2:10]3)=[O:12])[CH2:14][CH2:15]2)[O:20][N:72]=1

Participants

8

Reactant 5

HCID 319562,6-dichloro-N'-hydroxybenzene-1-carboximidamideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 285131921-(3,4-dihydroquinolin-1(2H)-ylcarbonyl)piperidine-4-carboxylic acid

Product 1

HCID 248529121-({4-[3-(2,6-Dichlorophenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl}carbonyl)-1,2,3,4-tetrahydroquinolineYield 37.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

0.3 g of 1-(3,4-dihydroquinolin-1(2H)-ylcarbonyl)piperidine-4-carboxylic acid, 11 ml of dimethylformamide, 0.67 g of O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium tetrafluoroborate, 0.028 g of 1-hydroxybenzotriazole, 0.91 ml of diisopropylethylamine and then 0.32 g of 2,6-dichloro-N′-hydroxybenzenecarboximidamide are introduced into a 100 ml round-bottomed flask. The reaction medium is stirred at ambient temperature for 1 h 30 and then heated at 95° C. for 20 hours. Water is added and the mixture is extracted with ethyl acetate. The organic phase is washed three times with water and dried over sodium sulfate and the solvent is evaporated under reduced pressure. The residue is chromatographed on silica gel with a heptane/ethyl acetate gradient from 0/1 to 1/1. 0.18 g of 1-({4-[3-(2,6-dichlorophenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl}carbonyl)-1,2,3,4-tetrahydroquinoline is obtained.

Workup

  1. temperatureheated at 95° C. for 20 hours
  2. extractionthe mixture is extracted with ethyl acetate
  3. washThe organic phase is washed three times with water
  4. dry with materialdried over sodium sulfate
  5. customthe solvent is evaporated under reduced pressure
  6. customThe residue is chromatographed on silica gel with a heptane/ethyl acetate gradient from 0/1 to 1/1

Sources & evidence

ORD record
ord-dbda138097cc4f2faacfcf8f1e139397
Source dataset
uspto-grants-2011_05
Patent number
US07947834B2

Reaction notes

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