Triethylamine → N-[3-(5-fluoro-3-pyridyl)acryloyl]-4-(4-diphenylmethyl-1-piperazinyl)butylamine

HRID 868334Notes

Reaction equation

HRID 868334 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]([OH:12])=O)[CH:5]=[N:6][CH:7]=1.C(N(CC)CC)C.ClC(OCC)=O.[C:26]1([CH:32]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[N:33]2[CH2:38][CH2:37][N:36]([CH2:39][CH2:40][CH2:41][CH2:42][NH2:43])[CH2:35][CH2:34]2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]([NH:43][CH2:42][CH2:41][CH2:40][CH2:39][N:36]2[CH2:37][CH2:38][N:33]([CH:32]([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH2:34][CH2:35]2)=[O:12])[CH:5]=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 27847502-Propenoic acid, 3-(5-fluoro-3-pyridinyl)-HCID 139569931-(4-Aminobutyl)-4-(diphenylmethyl)piperazine

Product 1

HCID 53948199N-[3-(5-fluoro-3-pyridyl)acryloyl]-4-(4-diphenylmethyl-1-piperazinyl)butylamineYield 36.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a stirred suspension of 0.29 g of 3-(5-fluoro-3-pyridyl)acrylic acid in 15 ml of dry tetrahydrofuran, 0.24 g of triethylamine is added at room temperature. The resulting solution is cooled to between -10° C. and -5° C., and a solution of 0.25 g of ethyl chloroformate in 2 ml of tetrahydrofuran is added slowly. After the mixture is stirred at the same temperature for 2 hours, a solution of 0.75 g of 4-(4-diphenylmethyl-1-piperazinyl)butylamine in 2 ml of dry tetrahydrofuran is added. The mixture is stirred for 1 hour at between -10° C. and -5° C. and then at room temperature overnight. The insoluble materials are filtered off, and the filtrate is concentrated. The residue is chromatographed on silica gel with chloroform-methanol (40:1) to give 0.3 g of the title compound. m.p. 128°-129° C. (recrystallized from toluene-hexane)

Workup

  1. additionis added at room temperature
  2. temperatureThe resulting solution is cooled to between -10° C. and -5° C.
  3. stirringThe mixture is stirred for 1 hour at between -10° C. and -5° C.
  4. customat room temperature
  5. customovernight
  6. filtrationThe insoluble materials are filtered off
  7. concentrationthe filtrate is concentrated
  8. customThe residue is chromatographed on silica gel with chloroform-methanol (40:1)

Sources & evidence

ORD record
ord-c4fed2bbb4004b5b9de3d30d94340a28
Source dataset
uspto-grants-1988_10
Patent number
US04778796

Reaction notes

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