Sodium Hydroxide → HCID 68428722, compound

HRID 2191302Notes

Reaction equation

HRID 2191302 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[C:20](=O)[C:19]2[CH:22]=[CH:23][C:24]([O:26][C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[CH:28]=3)=[N:25][C:18]=2[O:17][CH2:16][CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH-].[Na+].[Cl-].[NH4+]>C1COCC1.C(OCC)C.O>[CH2:7]([N:14]1[CH2:20][C:19]2[CH:22]=[CH:23][C:24]([O:26][C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[CH:28]=3)=[N:25][C:18]=2[O:17][CH2:16][CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 68428687HCID 68428687, compound

Product 1

HCID 68428722HCID 68428722, compoundYield 50.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21868444Ether tetrahydrofuranSolvent2×

Procedure

To a mixture of lithium aluminum hydride (0.079 g) and THF-diethyl ether solution (2.5 mL-2.5 mL) was added a solution of the compound obtained in step 1 (0.51 g) in THF-diethyl ether (2.5 mL-2.5 mL), and the resulting mixture was stirred at room temperature for 2 hr under a nitrogen atmosphere. 1N Aqueous sodium hydroxide solution (0.079 mL), saturated aqueous ammonium chloride (0.079 mL) and water (0.079 mL) were added, and the resulting mixture was stirred at room temperature for 3 hr. The precipitate was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (solvent gradient; 0→40% ethyl acetate/hexane) to give 4-benzyl-8-(3-chlorophenoxy)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (0.25 g, 49%) as a white powder.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 3 hr
  2. customThe precipitate was removed by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (solvent gradient; 0→40% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-4393ca6ed5e441a091f7a4155efd02ea
Source dataset
uspto-grants-2012_12
Patent number
US08329687B2

Reaction notes

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