Sodium Hydroxide → HCID 68429508, compound

HRID 2191293Notes

Reaction equation

HRID 2191293 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]=[CH:29][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+]>O.C1COCC1.C(OCC)C>[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]=[CH:29][CH:28]=3)=[N:25][C:18]=2[O:17][CH2:16][CH2:15]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydride2×HCID 68429387HCID 68429387, compound

Product 1

HCID 68429508HCID 68429508, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21868444Ether tetrahydrofuranSolvent

Procedure

To a mixture of lithium aluminum hydride (0.066 g) and THF-diethyl ether (2 mL-10 mL) was added the compound obtained in step 2 (0.40 g), and the resulting mixture was stirred at room temperature for 3 hr under a nitrogen atmosphere. Lithium aluminum hydride (0.066 g) was added again, and the resulting mixture was stirred at room temperature for 2 hr under a nitrogen atmosphere. 1N Aqueous sodium hydroxide solution (0.13 mL), saturated aqueous ammonium chloride (0.13 mL) and water (0.13 mL) were added, and the resulting mixture was stirred at room temperature for 4 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-phenoxy-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (0.19 g, 50%) as a white powder.

Workup

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

Sources & evidence

ORD record
ord-0a3a740dc5604adc97e4368d1752d5eb
Source dataset
uspto-grants-2012_12
Patent number
US08329687B2

Reaction notes

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