Water → HCID 21108215, compound

HRID 1766026Notes

Reaction equation

HRID 1766026 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl.[CH2:8]([N:11]([CH2:15][CH2:16][C:17]1[CH:18]=[CH:19][C:20]2[O:25][CH2:24][CH2:23][NH:22][C:21]=2[CH:26]=1)[CH2:12][CH2:13][CH3:14])[CH2:9][CH3:10].[Cl:27][CH2:28][C:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=[CH:31][CH:30]=1.O>CN(C=O)C>[ClH:27].[CH2:8]([N:11]([CH2:15][CH2:16][C:17]1[CH:18]=[CH:19][C:20]2[O:25][CH2:24][CH2:23][N:22]([CH2:28][C:29]3[C:38]4[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=4)[CH:32]=[CH:31][CH:30]=3)[C:21]=2[CH:26]=1)[CH2:12][CH2:13][CH3:14])[CH2:9][CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 68451-ChloromethylnaphthaleneHCID 11430Potassium CarbonateHCID 17848893HCID 17848893, compound

Product 1

HCID 21108215HCID 21108215, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (316 mg, 2.29 mmol) was added to a solution of 3,4-dihydro-6-[2-(N,N-dipropylamino)ethyl]-2H-1,4-benzoxazine hydrochloride (200 mg, 0.76 mmol) obtained in Example 134 and 1-chloromethyl naphthalene (400 mg, 2.29 mmol) in DMF (15 ml). After the reaction solution was stirred at room temperature for 2 hours, water was added to the reaction solution which was then extracted with ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate and concentrated. The residues were purified by silica gel column chromatography (developing solvent; hexane:ethyl acetate=3:1), treated with 4 N hydrochloric acid in ethyl acetate and crystallized from acetone-pentane, whereby the title compound (80 mg) was obtained as crystals with a mp of 177 to 178° C.

Workup

  1. extractionwas then extracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residues were purified by silica gel column chromatography (developing solvent; hexane:ethyl acetate=3:1)
  6. additiontreated with 4 N hydrochloric acid in ethyl acetate
  7. customcrystallized from acetone-pentane, whereby the title compound (80 mg)
  8. customwas obtained as crystals with a mp of 177 to 178° C.

Sources & evidence

ORD record
ord-3b59e56b3dff4bd4a0db54c6e46a6897
Source dataset
uspto-grants-2007_06
Patent number
US07229986B2

Reaction notes

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