Water → HCID 68430452, compound

HRID 2191305Notes

Reaction equation

HRID 2191305 reaction equation
[CH2:1]([N:8]1[C:14](=O)[C:13]2[CH:16]=[CH:17][C:18]([O:20][C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)=[N:19][C:12]=2[O:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[Cl-].[NH4+].O>C1COCC1.C(OCC)C>[CH2:1]([N:8]1[CH2:14][C:13]2[CH:16]=[CH:17][C:18]([O:20][C:21]3[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=3)=[N:19][C:12]=2[O:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 68429289HCID 68429289, compound

Product 1

HCID 68430452HCID 68430452, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 21868444Ether tetrahydrofuranSolvent2×

Procedure

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 (0.076 mL), saturated aqueous ammonium chloride (0.076 mL) and water (0.076 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-(4-chlorophenoxy)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (0.20 g, 42%) 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-f8393af36e8844f6a3e9bedd1b1f01ef
Source dataset
uspto-grants-2012_12
Patent number
US08329687B2

Reaction notes

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