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Chemical Structure| 120004-79-7 Chemical Structure| 120004-79-7

Structure of 120004-79-7

Chemical Structure| 120004-79-7

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Product Details of [ 120004-79-7 ]

CAS No. :120004-79-7
Formula : C13H16ClNO2
M.W : 253.72
SMILES Code : ClCCCCOC1=CC2=C(CCC(=O)N2)C=C1
MDL No. :MFCD07787529
InChI Key :SRMLSNBGMDJSJH-UHFFFAOYSA-N
Pubchem ID :10467467

Safety of [ 120004-79-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Application In Synthesis of [ 120004-79-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 120004-79-7 ]

[ 120004-79-7 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 6940-78-9 ]
  • [ 22246-18-0 ]
  • [ 120004-79-7 ]
  • [ 129722-34-5 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate;tetrabutylammomium bromide; In water; at 90℃; for 2 - 3h;Product distribution / selectivity; EXAMPLE 1. Preparation of the mixture of 7-(4-chlorobutoxy)-3,4-dihydro- 2(lH)quinolinone and 7-(4-bromobutoxy)-3,4-dihydro-2(lH)quinolinone; 7-Hydroxy-3,4-dihydro-2(lH)quinolinone (20 g), l-bromo-4-chlorobutane (85 ml), K2CO3 (17 g), tetrabutylamrnonium bromide (2.0 g) and water (200 ml) were charged. The mixture was heated to 90 0C and stirred for 3 hours at about 90 °C. The water phase was separated off. The organic phase was washed with 100 ml of water at about 90 0C. Hexane (400 ml) was added at about 20 °C. The mixture was stirred for about 20 hours at room temperature and then cooled to about 0 °C. The crystalline mixture of 7-(4-chlorobutoxy)-3,4-dihydro-2(lH)quinolinone and 7- (4-bromobutoxy)-3,4-dihydro-2(lH)quinolinone was filtered and washed with hexane (3*20 ml). The product was dried under reduced pressure at 40-50 °C. The yield was 30.5 g (95.6 percent). The product was a 85:15 mixture of Cl- and Br- compounds. The HPLC-purity was 98.2 percent, the amount of dimeric impurity was 1.1 percent, per weight.; EXAMPLE 2. Preparation of the mixture of 7-(4-chlorobutoxy)-3,4-dihydro-2(lH)quinolinone and 7-(4-bromobutoxy)-3,4-dihydro-2(lH)quinolinone7-Hydroxy-3,4-dihydro-2(lH)quinolinone (20 g), l-bromo-4-chlorobutane (42.4 ml), K2CO3 (17 g), tetrabutylammonium bromide (2.0 g) and water (200 ml) were charged. The mixture was heated to 90 °C and stirred for 2 hours at about 90 °C. The water phase was separated off. The organic phase was washed with 100 ml of water at about 9O0C. Hexane (300 ml) was added at 20-40 °C. The mixture was stirred for about 20 hours at room temperature. The crystalline mixture of 7-(4- chlorobutoxy)-3,4-dihydro-2(lH)quinolinone and 7-(4-bromobutoxy)-3,4-dihydro- 2(lH)quinolinone was filtered and washed with hexane (3*50 ml). The product was dried under reduced pressure at 40-50 °C. The yield was 30.5 g (95 percent) The product <n="9"/>was a 79.9:20.1 mixture of Cl- and Br-compounds. The HPLC-purity was 94.2 percent, the amount of dimeric impurity was 3.1 percent, per weight.
  • 2
  • 1-(2,3-dichlorophenyl)-piperazine hydrochloride [ No CAS ]
  • [ 120004-79-7 ]
  • [ 129722-34-5 ]
  • [ 129722-12-9 ]
YieldReaction ConditionsOperation in experiment
88% With N-ethyl-N,N-diisopropylamine; sodium iodide; In pentan-1-ol; at 100℃; for 5h;Heating / reflux;Product distribution / selectivity; EXAMPLE 4. Preparation of 7-[4-[4-(2,3-dichlorophenyl)-l-piperazinyl]- butoxy]-3,4-dihydro-2(lH)-qumolmone (aripiprazole); 7-(4-Chlorobutoxy)-3,4-dihydro-2(lH)quinolinone and 7-(4-bromobutoxy)- 3,4-dihydro-2(lH)quinolinone (79.9:20.1 mixture, 6.0 g), sodium iodide (4.9 g), diisopropylethylamine (4.6 ml) and l-(2,3-dichlorophenyl)piperazine (6.1 g) in 45 ml of 1-pentanol were charged. The mixture was kept at about 100 °C for 5 hours. The mixture was cooled and water (60 ml) and 50 percent NaOH (6 ml) were added. The water phase was separated off. Water (10 m) was added to the organic phase and the solution was cooled to room temperature. The crystalline 7-[4-[4-(2,3- dichlorophenyl)-l-piperazinyl]-butoxy]-3,4-dihydro-2(lH)-quinolinone (aripiprazole) was filtered and washed with 1-pentanol and isopropanol. The product was dried under reduced pressure at 80-90 0C. The yield was 8.6 g (88 percent) and the HPLC-purity was 99 percent.The raw product (3.0 g), ethanol (48 ml) and water (10 ml) were charged. The solution was refluxed until all dissolved. Water (10 ml) was added and the solution was cooled to room temperature. The crystalline compound was filtred and washed <n="10"/>with ethanol:water mixture. The product was dried under reduced pressure at 80-90 °C. The yield was 2.8 g (93 percent) and the HPLC-purity was 99.7 percent.
83% EXAMPLE 3. Preparation of 7-[4-[4-(2,3-dichlorophenyl)-l-piperazinyl]- butoxy]-3,4-dihydro-2(lH)-quinolinone (aripiprazole).; 7-(4-Chlorobutoxy)-3,4-dihydro-2(lH)quinolinone and 7-(4-bromobutoxy)-3,4-dihydro-2(lH)quinolinone ( 89.4:10.6 mixture, 2.0 g), sodium iodide (1.8 g) and acetonitrile (60 ml) were charged. The mixture was refluxed for 17 hours and then filtered. l-(2,3-Dichlorophenyl)rhoiperazine hydrochloride (2.3 g) and triethylamine (3.7 ml) were added to the solution. The mixture was refluxed for 23 hours. Water (2.0 ml) was added and the solution was cooled to room temperature and stirred for 4 hours at room temperature. The crystalline 7-[4-[4-(2,3-dichlorophenyl)-l- piperazinyl]-butoxy]-3,4-dihydro-2(lH)-quinolinone (aripiprazole) was filtered and washed with acetonitrile. The product was dried under reduced pressure at 40-50 0C. The yield of aripiprazole was 2.89 g (83 percent) and HPLC-purity was 99.4 percent.
 

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