Water → (1S)-1-{2-[(2R)-4-(6-fluoro-1-naphthyl)-2-methylpiperazinyl]ethyl}-3,4-dihydro-1H-2-benzopyran-6-amine

HRID 2056766ノート

反応式

HRID 2056766 の反応式
C1(C(C2C=CC=CC=2)=[N:8][C:9]2[CH:10]=[CH:11][C:12]3[C@H:17]([CH2:18][CH2:19][N:20]4[CH2:25][CH2:24][N:23]([C:26]5[C:35]6[C:30](=[CH:31][C:32]([F:36])=[CH:33][CH:34]=6)[CH:29]=[CH:28][CH:27]=5)[CH2:22][C@H:21]4[CH3:37])[O:16][CH2:15][CH2:14][C:13]=3[CH:38]=2)C=CC=CC=1.C([O-])(=O)C.[Na+].Cl.NO.O>CO>[F:36][C:32]1[CH:31]=[C:30]2[C:35](=[CH:34][CH:33]=1)[C:26]([N:23]1[CH2:24][CH2:25][N:20]([CH2:19][CH2:18][C@H:17]3[C:12]4[CH:11]=[CH:10][C:9]([NH2:8])=[CH:38][C:13]=4[CH2:14][CH2:15][O:16]3)[C@H:21]([CH3:37])[CH2:22]1)=[CH:27][CH:28]=[CH:29]2

参加物

6

反応物 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 86596019(1S)-N-(diphenylmethylene)-1-{2-[(2R)-4-(6-fluoro-1-naphthyl)-2-methylpiperazinyl]ethyl}-3,4-dihydro-1H-2-benzopyran-6-amine

生成物 1

HCID 69307771(1S)-1-{2-[(2R)-4-(6-fluoro-1-naphthyl)-2-methylpiperazinyl]ethyl}-3,4-dihydro-1H-2-benzopyran-6-amine

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of (1S)-N-(diphenylmethylene)-1-{2-[(2R)-4-(6-fluoro-1-naphthyl)-2-methylpiperazinyl]-ethyl}-3,4-dihydro-1H-2-benzopyran-6-amine (1.46 g, 2.5 mmol) in methanol (25 mL) was added sodium acetate (0.28 g, 2.65 mmol) and hydroxylamine hydrochloride (0.194 g, 2.8 mmol), and the mixture stirred at room temperature under nitrogen for 18 h. Water was added and extracted with dichloromethane. The combined organic extracts were dried (MgSO4), filtered and evaporated in vacuo. The crude product was purified by flash chromatography on silica, eluting with methanol/ethyl acetate (0:100 to 15:85), to yield (1S)-1-{2-[(2R)-4-(6-fluoro-1-naphthyl)-2-methylpiperazinyl]ethyl}-3,4-dihydro-1H-2-benzopyran-6-amine. M+H=420.

後処理

  1. extractionextracted with dichloromethane
  2. dry with materialThe combined organic extracts were dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe crude product was purified by flash chromatography on silica
  6. washeluting with methanol/ethyl acetate (0:100 to 15:85)

出典と根拠

ORDレコード
ord-01e32e5160f64d4d8926680f1601644f
出典データセット
uspto-grants-2008_02
特許番号
US07335660B2

反応ノート

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