Hydrogen Bromide → 6-Chloro-3-{1-[1,3-dihydro-2-oxo-2H-benzimidazol-1-ylpropyl]-4-piperidyl}-1,2-benzisoxazole hydrobromide

HRID 223259ノート

反応式

HRID 223259 の反応式
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[C:11]3[CH:12]=[CH:13][C:14]([Cl:16])=[CH:15][C:10]=3[O:9][N:8]=2)[CH2:3][CH2:2]1.Cl[CH2:18][CH2:19][CH2:20][N:21]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[NH:23][C:22]1=[O:30].C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+].[BrH:39]>CC(CC(=O)C)C.C(O)C>[BrH:39].[Cl:16][C:14]1[CH:13]=[CH:12][C:11]2[C:7]([CH:4]3[CH2:3][CH2:2][N:1]([CH2:18][CH2:19][CH2:20][N:21]4[C:25]5[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=5[NH:23][C:22]4=[O:30])[CH2:6][CH2:5]3)=[N:8][O:9][C:10]=2[CH:15]=1

参加物

8

反応物 5

HCID 260Hydrogen BromideHCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 18104191-(3-chloropropyl)-1,3-dihydro-2H-benzimidazol-2-oneHCID 130764306-Chloro-3-(piperidin-4-yl)benzo[d]isoxazole

生成物 1

HCID 130784036-Chloro-3-{1-[1,3-dihydro-2-oxo-2H-benzimidazol-1-ylpropyl]-4-piperidyl}-1,2-benzisoxazole hydrobromide収率 53%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒2 回HCID 7909Methyl Isobutyl Ketone溶媒

実験手順

A stirred mixture, under nitrogen, of 18.9 g of 3-(4-piperidyl)-6-chloro-1,2-benzisoxazole, 16.9 g of 1-(3-chloropropyl)-1,3-dihydro-2H-benzimidazol-2-one, 17.0 g of anhydrous sodium carbonate and 1.33 g of pulverized potassium iodide in 1000 ml of 2-methyl-4-pentanone was heated under reflux for 6 hrs. The solvent was removed and the residue was partitioned between 500 ml of dichloromethane and 250 ml of water. The organic phase was separated, washed three times with brine, dried under anhydrous sodium sulfate and concentrated, first at aspirator pressure in a 100° bath, then with the high-vacuum pump attached to yield an oil. The oil was dissolved in 150 ml of ethanol. The solution was cooled and stirred, while 50 ml of ethanol, freshly saturated with gaseous hydrogen bromide, was added over a 5-min period. After stirring 1 hr more in the cold, the salt was collected, filtered, washed twice with ethanol and dried to afford 16.0 g (53%) of product, mp 231°-237° dec.

後処理

  1. temperatureunder reflux for 6 hrs
  2. customThe solvent was removed
  3. customthe residue was partitioned between 500 ml of dichloromethane and 250 ml of water
  4. customThe organic phase was separated
  5. washwashed three times with brine
  6. customdried under anhydrous sodium sulfate
  7. concentrationconcentrated, first at aspirator pressure in a 100° bath
  8. customto yield an oil
  9. temperatureThe solution was cooled
  10. additionwas added over a 5-min period
  11. customwas collected
  12. filtrationfiltered
  13. washwashed twice with ethanol
  14. customdried

出典と根拠

ORDレコード
ord-5ad1f4f0edef412bb0f14fbfb422925d
出典データセット
uspto-grants-1982_10
特許番号
US04352811

反応ノート

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