Water → HCID 11230046, compound

HRID 851933Notes

Reaction equation

HRID 851933 reaction equation
[H-].[Na+].[NH:3]1[C:9](=[O:10])[CH2:8][CH2:7][CH2:6][C:5]2[CH:11]=[CH:12][CH:13]=[CH:14][C:4]1=2.[CH3:15][O:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Cl)=[CH:19][CH:18]=1.O.[CH3:26][N:27]([CH:29]=[O:30])C>>[OH:16][NH:3][C:9](=[O:10])[CH2:8][CH:7]1[C:29](=[O:30])[NH:27][C:26]2[CH:11]=[CH:12][CH:13]=[CH:14][C:4]=2[CH2:5][CH2:6]1.[CH2:15]([O:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][N:3]2[C:9](=[O:10])[CH2:8][CH2:7][CH2:6][C:5]3[CH:11]=[CH:12][CH:13]=[CH:14][C:4]2=3)=[CH:19][CH:18]=1)[CH3:26]

Participants

7

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 2485801,3,4,5-Tetrahydro-2H-1-benzazepin-2-one

Product 2

HCID 11230046HCID 11230046, compoundHCID 69009900HCID 69009900, compound

Conditions

Temperature
0 °C

Procedure

NaH (60% in mineral oil) (1.86 mmol) is added to a solution a 1,3,4,5-tetrahydro-benzo[b]azepin-2-one (1.55 mmol) in 5 mL of DMF at 0° C., After stirring at 0° C. for 15 minutes, the mixture is allowed to warm up to room temperature. p-Methoxybenzyl chloride (1.94 mmol) is added to the mixture. After stirring at room temperature for 16 hours, the mixture is poured into 50 mL of water and extracted with EtOAc (3×25 mL). The organic layer are combined, washed with brine and dried over MgSO4. After removing the solvent under reduced pressure, the residue is purified by flash column chromatography (silica gel) to provide the desired product 1-(4-ethoxy-benzyl)-1,3,4,5-tetrahydro-benzo[b]azepin-2-one as white solid. Yield: 90%. MS: (ES+): 282.1 [M+1].

Workup

  1. temperatureto warm up to room temperature
  2. stirringAfter stirring at room temperature for 16 hours
  3. extractionextracted with EtOAc (3×25 mL)
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. customAfter removing the solvent under reduced pressure
  7. customthe residue is purified by flash column chromatography (silica gel)

Sources & evidence

ORD record
ord-8147744aa4574fe28fe99b395a865102
Source dataset
uspto-grants-2007_08
Patent number
US07253164B2

Reaction notes

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