Triethylamine → HCID 21890169, compound

HRID 721570Notes

Reaction equation

HRID 721570 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1.C(N(CC)CC)C.ClC(Cl)(O[C:34](=[O:40])OC(Cl)(Cl)Cl)Cl.[N:42]1([CH2:48][CH2:49][NH2:50])[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]1>C(Cl)(Cl)Cl.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:22]=[CH:21][C:19]([NH:20][C:34]([NH:50][CH2:49][CH2:48][N:42]2[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]2)=[O:40])=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 33944N-(2-Aminoethyl)piperidineHCID 94429TriphosgeneHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]aniline

Product 1

HCID 21890169HCID 21890169, compoundYield 78.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

4-[(6,7-Dimethoxy-4-quinolyl)oxy]aniline (100 mg) was dissolved in chloroform (10 ml) and triethylamine (1 ml) to prepare a solution. A solution of triphosgene (151 mg) in chloroform was then added to the solution, and the mixture was stirred at room temperature for 10 min. Next, 2-piperidino-1-ethanamine (65 mg) was added thereto, and the mixture was further stirred at room temperature for one hr. Water was added to stop the reaction, and the reaction solution was then extracted with chloroform, followed by concentration. The residue was purified on a column using chloroform/methanol to give the title compound (119 mg, yield 78%).

Workup

  1. stirringthe mixture was further stirred at room temperature for one hr
  2. customthe reaction
  3. extractionthe reaction solution was then extracted with chloroform
  4. concentrationfollowed by concentration
  5. customThe residue was purified on a column

Sources & evidence

ORD record
ord-efe2a77c2dc24e5ebb3b27906ce40a82
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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