Triethylamine → HCID 17773153, compound

HRID 635302Notes

Reaction equation

HRID 635302 reaction equation
[N:1]1[CH:2]=[C:3]([CH2:10][CH2:11][C:12](O)=O)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.Cl.[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)=[CH:19][CH:18]=1.C(N(CC)CC)C.P(C#N)(OCC)(OCC)=O>CN(C)C=O.O.O1CCCC1>[Cl:16][C:17]1[CH:18]=[CH:19][C:20]([N:23]2[CH2:28][CH2:27][N:26]([CH2:12][CH2:11][CH2:10][C:3]3[N:4]4[CH:9]=[CH:8][CH:7]=[CH:6][C:5]4=[N:1][CH:2]=3)[CH2:25][CH2:24]2)=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 30847201-(4-Chlorophenyl)piperazine HydrochlorideHCID 10511867HCID 10511867, compound

Product 1

HCID 17773153HCID 17773153, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of 3-(imidazo[1,2-a]pyridin-3-yl)propionic acid (4 g) synthesized according to the method described in Japanese Patent Unexamined Publication No. 189179/1983, 1-(4-chlorophenyl)piperazine hydrochloride (4.9 g) and triethylamine (5.9 ml) in dimethylformamide was added dropwise diethyl cyanophosphate (3.8 ml) under ice-cooling with stirring, and the mixture was stirred for 3 hours. After the completion of the reaction, the reaction mixture was concentrated, extracted with chloroform, washed with water and dyed over magnesium sulfate. The solution was concentrated under reduced pressure, and lithium aluminum hydride was added to a solution of the obtained 4-(4-chlorophenyl)-1-(3-(imidazo[1,2-a]pyridin-3-yl)propionyl)piperazine in tetrahydrofuran under ice-cooling with stirring, and the mixture was stirred at room temperature for 1 hour. After the completion of the reaction, the reaction mixture was treated with a mixed solvent of water-tetrahydrofuran and filtered through celite. The filtrate was concentrated under reduced pressure the obtained residue was subjected to silica gel column chromatography to give 3-(3-(4-(4-chlorophenyl)piperazin-1-yl)propyl)imidazo[1,2-a]pyridine. This compound was dissolved in a mixture of ethanol (20 ml) and conc. hydrochloric acid (20 ml) and reduced in the presence of 10% palladium-carbon (1 g) in an autoclave at 70° C. and 50 atm. After the completion of the reaction, the reaction mixture was filtered through celite. The filtrate was concentrated under reduced pressure and the obtained residue was subjected to silica gel column chromatography to give 3-(3-(4-(4-chlorophenyl)piperazin-1-yl)propyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine, m.p. 95-97° C. (m.p. as oxalate).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 3 hours
  3. customAfter the completion of the reaction
  4. concentrationthe reaction mixture was concentrated
  5. extractionextracted with chloroform
  6. washwashed with water
  7. concentrationThe solution was concentrated under reduced pressure, and lithium aluminum hydride
  8. additionwas added to a solution of the obtained 4-(4-chlorophenyl)-1-(3-(imidazo[1,2-a]pyridin-3-yl)propionyl)piperazine in tetrahydrofuran under ice-
  9. temperaturecooling
  10. stirringwith stirring
  11. stirringthe mixture was stirred at room temperature for 1 hour
  12. customAfter the completion of the reaction
  13. filtrationfiltered through celite
  14. concentrationThe filtrate was concentrated under reduced pressure the obtained residue

Sources & evidence

ORD record
ord-aeff79dd08c04af3922fbe52045ef459
Source dataset
uspto-grants-2001_02
Patent number
US06187774B1

Reaction notes

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