Triethylamine → HCID 13487103、化合物

HRID 1975407ノート

反応式

HRID 1975407 の反応式
[C:1]([Cl:5])(=O)[CH2:2][CH3:3].[CH3:6][O:7][C:8]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:9]=1[CH2:10][CH2:11][C@H:12]([NH:19][CH2:20][CH2:21][CH3:22])[C@@H:13]2[CH3:18].C(N(CC)CC)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC.C1COCC1>[ClH:5].[CH3:6][O:7][C:8]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:9]=1[CH2:10][CH2:11][C@H:12]([N:19]([CH2:1][CH2:2][CH3:3])[CH2:20][CH2:21][CH3:22])[C@@H:13]2[CH3:18]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 13755574HCID 13755574、化合物HCID 21226445Aluminium lithium hydride

生成物 1

HCID 13487103HCID 13487103、化合物収率 42.8%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

Propionyl chloride (0.49 g, 5.2 mmol) in dry ether (10 ml) was added to a solution of cis-5-methoxy-1-methyl-2-(n-propylamino)tetralin (350 mg, 1.5 mmol) and triethylamine (0.49 g, 4.9 mmol) in dry ether (80 ml). After 30 min. at room temperature the reaction mixture was filtered and the ether was evaporated. The resulting crude amide was passed through an alumina column eluted with ether. The purified amide dissolved in dry THF (20 ml) was added to a suspension of LiAlH4 (1.0 g, 26 mmol) in dry THF (30 ml) under N2. After stirring under reflux for 3 h, the reaction mixture was hydrolyzed, the precipitate was filtered off and the solvent was evaporated. The oily residue was chromatographed on an alumina column with ether-light petroleum (1:1) as eluant. The hydrochloride was prepared and recrystallized from EtOH-ether to give 200 mg (42%) of title product: mp 170.5°-171.5° C.; GC (215° C.) isomeric purity >95%, retention time 2.45 min; NMR (MeOH-d4) δ1.05 (t,6H) δ1.32 (d,3H) δ1.64-3.66 (m,14H), δ3.80 (s,3H), δ6.71-6.82 (m,2H), δ7.10-7.20 (m,1H); MS (70 eV) m/z 275 (28%), 246 (100%), 176 (69%).

後処理

  1. filtrationAfter 30 min. at room temperature the reaction mixture was filtered
  2. customthe ether was evaporated
  3. washeluted with ether
  4. dissolutionThe purified amide dissolved in dry THF (20 ml)
  5. temperatureunder reflux for 3 h
  6. filtrationthe precipitate was filtered off
  7. customthe solvent was evaporated
  8. customThe oily residue was chromatographed on an alumina column with ether-light petroleum (1:1) as eluant
  9. customThe hydrochloride was prepared
  10. customrecrystallized from EtOH-ether

出典と根拠

ORDレコード
ord-07a142feb20742f28882542b0c7a0ee0
出典データセット
uspto-grants-1994_02
特許番号
US05286747

反応ノート

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