Triethylamine → HCID 131719221, compound

HRID 2259899Notes

Reaction equation

HRID 2259899 reaction equation
[CH3:1][C:2]1[C:7](=[O:8])[C:6]2[CH:9]=[CH:10][CH:11]=[C:12]([C:13]([Cl:15])=[O:14])[C:5]=2[O:4][C:3]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[CH3:22][O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[N:30]1[CH2:35][CH2:34][N:33]([CH2:36][CH2:37][CH2:38][NH2:39])[CH2:32][CH2:31]1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[OH2:4].[ClH:15].[ClH:15].[CH3:22][O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[N:30]1[CH2:31][CH2:32][N:33]([CH2:36][CH2:37][CH2:38][NH:39][C:13]([C:12]2[C:5]3[O:4][C:3]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)=[C:2]([CH3:1])[C:7](=[O:8])[C:6]=3[CH:9]=[CH:10][CH:11]=2)=[O:14])[CH2:34][CH2:35]1.[CH3:22][O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[N:30]1[CH2:31][CH2:32][N:33]([CH2:36][CH2:37][CH2:38][NH:39][C:13]([C:12]2[C:5]3[O:4][C:3]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)=[C:2]([CH3:1])[C:7](=[O:8])[C:6]=3[CH:9]=[CH:10][CH:11]=2)=[O:14])[CH2:34][CH2:35]1.[ClH:15].[ClH:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 104672591-(3-Aminopropyl)-4-(2-methoxyphenyl)piperazineHCID 13122092HCID 13122092, compound

Product 1

HCID 131719221HCID 131719221, compoundYield 149.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 4.48 g of 3-methyl-4-oxo-2-phenyl-4H-1-benzopyran-8-carbonyl chloride in 40 ml of chloroform was added dropwise over a period of 10 minutes at ambient temperature to a solution of 3.74 g of 3-[4-(2-methoxyphenyl)-1-piperazinyl]propylamine (prepared as in British Patent No. 2,161,807) and 1.97 g of triethylamine in 50 ml of chloroform. After stirring for 2 hours, the solution was washed first with 0.5N aqueous hydrochloric acid solution, secondly with a saturated aqueous sodium bicarbonate solution and finally with water. The chloroform solution was dried on anhydrous sodium sulfate and the solvent was evaporated off in vacuo. The residue was worked up as described in Example 11 to give 6.67 g of the title compound, m.p. (177) 182°-186° C. This represents an alternative route to the product of Example 11.

Workup

  1. washthe solution was washed first with 0.5N aqueous hydrochloric acid solution, secondly with a saturated aqueous sodium bicarbonate solution and finally with water
  2. dry with materialThe chloroform solution was dried on anhydrous sodium sulfate
  3. customthe solvent was evaporated off in vacuo

Sources & evidence

ORD record
ord-eb25339951f945568df09efc5fd4f3d7
Source dataset
uspto-grants-1995_12
Patent number
US05474994

Reaction notes

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