Trifluoroacetic acid → 5-Methoxy-N,N-dipropyl-3,4-dihydro-2H-1-benzopyran-3-amine

HRID 981673ノート

反応式

HRID 981673 の反応式
[CH3:1][O:2][C:3]1[C:8]2[CH2:9][C:10](=O)[CH2:11][O:12][C:7]=2[CH:6]=[CH:5][CH:4]=1.[CH2:14]([NH:17][CH2:18][CH2:19][CH3:20])[CH2:15][CH3:16].FC(F)(F)C(O)=O>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[C:8]2[CH2:9][CH:10]([N:17]([CH2:18][CH2:19][CH3:20])[CH2:14][CH2:15][CH3:16])[CH2:11][O:12][C:7]=2[CH:6]=[CH:5][CH:4]=1

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 8902DipropylamineHCID 117690965-methoxy-3,4-dihydro-2H-1-benzopyran-3-one

生成物 1

HCID 30825975-Methoxy-N,N-dipropyl-3,4-dihydro-2H-1-benzopyran-3-amine

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A mixture of 6.4 g of 5-methoxy-3,4-dihydro-2H-[1]-benzopyran-3-one, 30 ml of dipropylamine, 0.5 ml of trifluoroacetic acid and 200 ml of toluene is refluxed in a Dean-Stark apparatus for 3 hours. The solution concentrated in vacuo and the residue is added to a solution of 7 g of sodium cyanoborohydride in 160 ml of ethanol and 40 ml of acetic acid. After 15 minutes at room temperature most of the solvent is removed in vacuo. The residue is dissolved in 6N hydrochloric acid and washed with ether. The aqueous layer is made basic and the product is extracted with ether. The aqueous layer is made basic and the product is extracted with ether. The ether layer is dried over magnesium sulfate and the solvent is removed in vacuo, to afford 5-methoxy-3,4-dihydro-N,N-dipropyl-2H-[1]-benzopyran-3-amine which is treated with ethanolic hydrochloric acid to afford 5-methoxy-3,4-di-hydro-N,N-dipropyl-2H-[1]-benzopyran-3-amine hydrochloride, m.p. 219°-221°.

後処理

  1. temperatureis refluxed in a Dean-Stark apparatus for 3 hours
  2. concentrationThe solution concentrated in vacuo
  3. additionthe residue is added to a solution of 7 g of sodium cyanoborohydride in 160 ml of ethanol and 40 ml of acetic acid
  4. customAfter 15 minutes at room temperature most of the solvent is removed in vacuo
  5. dissolutionThe residue is dissolved in 6N hydrochloric acid
  6. washwashed with ether
  7. extractionthe product is extracted with ether
  8. extractionthe product is extracted with ether
  9. dry with materialThe ether layer is dried over magnesium sulfate
  10. customthe solvent is removed in vacuo

出典と根拠

ORDレコード
ord-2a2bd106b67946b4aef69d56666d14a9
出典データセット
uspto-grants-1991_02
特許番号
US04992465

反応ノート

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