Potassium Carbonate → N-[(1-Benzyl-4-piperidyl)methy] 3,4-dihydro-2 H-[1,3]oxazino[3,2-a]indole-10-Carboxamide

HRID 1458602ノート

反応式

HRID 1458602 の反応式
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH:15][C:16]([C:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[NH:20][CH:19]=2)=[O:17])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:28][CH2:29][CH2:30][OH:31].C([O-])(O)=O.[Na+].C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH:15][C:16]([C:18]2[C:26]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[N:20]3[CH2:28][CH2:29][CH2:30][O:31][C:19]=23)=[O:17])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 516892Sodium BicarbonateHCID 19599446N-[(l-benzyl-4-piperidyl)methyl] indole-3-carboxamide

生成物 1

HCID 19599417N-[(1-Benzyl-4-piperidyl)methy] 3,4-dihydro-2 H-[1,3]oxazino[3,2-a]indole-10-Carboxamide収率 15.4%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

A stirred suspension of N-[(l-benzyl-4-piperidyl)methyl] indole-3-carboxamide (17.5 g, 0.050 mole) in chloroform (250 ml) was treated with 3-bromo-1-propanol (10.1 ml, 0.11 mole) and N-chlorosuccinimde (8.7 g, 0.065 mole) at room temperature and a clear solution was obtained in 15 minutes. After 1 h the reaction mixture darkened in colour from pale yellow to orange and temperature rose to 38° C. After a further 1 h the reaction mixture was treated with 10% NaHCO3 solution and the chloroform layer separated, dried (Na2SO4) and concentrated in vacuo to leave a yellow oil, which was chromatographed on silica gel eluting with 3% methanol/chloroform. The 2-(3-bromopropoxy)indole intermediate was dissolved in acetone (400 ml), treated with anhydrous potassium carbonate (11 g, 0.80 mole) and stirred at room temperature for 20 h. The reaction mixture was concentrated in vacuo and the residue treated with water (200 ml) and extracted with chloroform (2×250 ml). The combined extracts were dried (Na2 SO4), concentrated in vacuo and the residue chromatographed on silica gel eluting with 5% methanol/chloroform to afford the title compound (E20) as a pale yellow oil (3.1 g, 15%). This was converted to its oxalate salt and crystallised from acetone as a white solid mp 169°-170° C.

後処理

  1. customa clear solution was obtained in 15 minutes
  2. customrose to 38° C
  3. customthe chloroform layer separated
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customto leave a yellow oil, which
  7. customwas chromatographed on silica gel eluting with 3% methanol/chloroform
  8. dissolutionThe 2-(3-bromopropoxy)indole intermediate was dissolved in acetone (400 ml)
  9. concentrationThe reaction mixture was concentrated in vacuo
  10. additionthe residue treated with water (200 ml)
  11. extractionextracted with chloroform (2×250 ml)
  12. customThe combined extracts were dried (Na2 SO4)
  13. concentrationconcentrated in vacuo
  14. customthe residue chromatographed on silica gel eluting with 5% methanol/chloroform

出典と根拠

ORDレコード
ord-36ca5b93a6a44176925f5802df98e8cc
出典データセット
uspto-grants-1998_12
特許番号
US05852014

反応ノート

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