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

HRID 2056766Notes

Reaction equation

HRID 2056766 reaction equation
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

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-01e32e5160f64d4d8926680f1601644f
Source dataset
uspto-grants-2008_02
Patent number
US07335660B2

Reaction notes

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