Benzyl Bromide → HCID 68495096, compound

HRID 1944226Notes

Reaction equation

HRID 1944226 reaction equation
[CH2:1]([O:8][C:9]1[C:20]([O:21][CH3:22])=[CH:19][C:12]2[NH:13][C:14](=[O:18])[CH2:15][CH2:16][CH2:17][C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(Cl)C1C=CC=CC=1>CN(C=O)C.O>[CH2:25]([N:13]1[C:14](=[O:18])[CH2:15][CH2:16][CH2:17][C:11]2[CH:10]=[C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:20]([O:21][CH3:22])=[CH:19][C:12]1=2)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 59471518HCID 59471518, compound

Product 1

HCID 68495096HCID 68495096, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 7-benzyloxy-8-methoxy-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one (297 mg, 1.0 mmol) and NaH (80 mg, 2 mmol) was stirred in DMF (5 mL) for 10 minute at rt and the appropriate benzyl bromide or benzyl chloride (1.1 mmol) added. The mixture was stirred o/n at rt. After addition of water the organics extracted with ethyl acetate, washed with water, brine, dried (MgSO4), filtered and concentrated. The crude yellow oil was purified by flash chromatography (hexane/EtOAc 1:0 to 1:1) and the resultant solid stirred in Et2O, filtered and dried under vacuum.

Workup

  1. extractionorganics extracted with ethyl acetate
  2. washwashed with water, brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude yellow oil was purified by flash chromatography (hexane/EtOAc 1:0 to 1:1)
  7. stirringthe resultant solid stirred in Et2O
  8. filtrationfiltered
  9. customdried under vacuum

Sources & evidence

ORD record
ord-b24d8c529d9c4f559524796ff32d18c2
Source dataset
uspto-grants-2013_03
Patent number
US08394825B2

Reaction notes

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