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

HRID 2056766노트

반응식

HRID 2056766 반응식
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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-01e32e5160f64d4d8926680f1601644f
출처 데이터셋
uspto-grants-2008_02
특허 번호
US07335660B2

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