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Phosphorus oxide (P4O10) → 1-Chloromethyl-6-methoxy-3,4-dihydro-isoquinolinium chloride

HRID 1726434
ノート
印刷プレビュー

反応式

HRID 1726434 の反応式
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[Cl:15][CH2:16][C:17]([NH:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=1)=O>CCOCC>[Cl-:15].[Cl:15][CH2:16][C:17]1[C:27]2[C:22](=[CH:23][C:24]([O:28][CH3:29])=[CH:25][CH:26]=2)[CH2:21][CH2:20][NH+:19]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 14812Phosphorus oxide (P4O10)2 回HCID 214755Acetamide, 2-chloro-N-(m-methoxyphenethyl)-

生成物 1

HCID 666570771-Chloromethyl-6-methoxy-3,4-dihydro-isoquinolinium chloride

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

実験手順

Two equiv. of P2O5 (12.9 g) was boiled in xylenes (180 mL) as a 0.25 M solution. The crude product from Step 1 above was also first boiled in xylenes (45 mL) to make a 0.5 M solution, and it was then added dropwise via an addition funnel to the P2O5 solution. The mixture was stirred and heated at reflux for 1 h. The reaction was then cooled to RT and the xylenes decanted off at this point. The flask was then placed in an ice bath and stirred while ice, water, EtOAc, and finally 4 M NaOH were added carefully until the pH>12. Reaction was kept <25° C. until pH=12 was reached. The reaction was then extracted with EtOAc (3×). The combined organic extracts were dried over MgSO4 and concentrated to give a dark solution. This was cooled in an ice bath while 400 mL of cold Et2O was added followed by 100 mL of cold HC1/Et2O. A precipitate formed and was filtered away, washing with Et2O. The solid was immediately placed on high vac for 2 h to give the target product as a colored foamy solid. This crude product was directly used in the next step without further purification.

後処理

  1. temperatureheated
  2. temperatureat reflux for 1 h
  3. customthe xylenes decanted off at this point
  4. customThe flask was then placed in an ice bath
  5. stirringstirred while ice, water, EtOAc, and finally 4 M NaOH
  6. additionwere added carefully until the pH>12
  7. customReaction
  8. customwas kept <25° C. until pH=12
  9. extractionThe reaction was then extracted with EtOAc (3×)
  10. dry with materialThe combined organic extracts were dried over MgSO4
  11. concentrationconcentrated
  12. customto give a dark solution
  13. additionwas added
  14. customA precipitate formed
  15. filtrationwas filtered away
  16. washwashing with Et2O

出典と根拠

ORDレコード
ord-36a31562957c499fa3c16088768acd61
出典データセット
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07491794B2

反応ノート

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