Sodium hydride → 1-(2-{4-[2-(4-Methanesulfonyl-phenyl)-6-methoxy-naphthalen-1-yloxy]-phenoxy}-ethyl)-azepine Hydrochloride

HRID 732789Notes

Reaction equation

HRID 732789 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([O:21][CH3:22])[CH:17]=3)[C:12]=2[O:23][C:24]2[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].Cl.[N:32](=[CH:40][CH2:41]Cl)[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][Cl:39].[H-].[Na+]>CN(C)C=O>[ClH:39].[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([O:21][CH3:22])[CH:17]=3)[C:12]=2[O:23][C:24]2[CH:25]=[CH:26][C:27]([O:30][CH2:41][CH2:40][N:32]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=[CH:33]3)=[CH:28][CH:29]=2)=[CH:9][CH:10]=1)(=[O:3])=[O:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 534452772-(hexamethyleneimino)ethyl chloride HClHCID 685159634-[2-(4-Methanesulfonyl-phenyl)-6-methoxy-naphthalen-1-yloxy]-phenol

Product 1

HCID 685159301-(2-{4-[2-(4-Methanesulfonyl-phenyl)-6-methoxy-naphthalen-1-yloxy]-phenoxy}-ethyl)-azepine HydrochlorideYield 71.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Stir a solution of 4-[2-(4-methanesulfonyl-phenyl)-6-methoxy-naphthalen-1-yloxy]-phenol (160 mg, 0.39 mmol), 2-(hexamethyleneimino)-ethyl chloride hydrochloride (140 mg, 0.69 mmol), 60% sodium hydride (47 mg, 1.18 mmol) and N,N-dimethylformamide (2 mL) for 18 hours at ambient temperature, then evaporate under reduced pressure. Dissolve the residue in dichloromethane and wash with water, dry with solid magnesium sulfate and chromatograph on silica gel with dichloromethane/methanol mixtures. Combine the fractions containing product and add 1N hydrogen chloride in diethyl ether (0.30 mL). Concentrate the resulting solution under reduced pressure to give 160 mg of the title compound (69%). Mass spectrum (ion spray): m/z=546 (M+H).

Workup

  1. customevaporate under reduced pressure
  2. dissolutionDissolve the residue in dichloromethane
  3. washwash with water
  4. dry with materialdry with solid magnesium sulfate and chromatograph on silica gel with dichloromethane/methanol mixtures
  5. additionCombine the fractions containing product
  6. additionadd 1N hydrogen chloride in diethyl ether (0.30 mL)
  7. concentrationConcentrate the resulting solution under reduced pressure

Sources & evidence

ORD record
ord-5e6451b196b345fdbd62d9e0a449de80
Source dataset
uspto-grants-2009_09
Patent number
US07585977B2

Reaction notes

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