Water → HCID 18998289, compound

HRID 2260489Notes

Reaction equation

HRID 2260489 reaction equation
P(Cl)(Cl)(Cl)=O.[CH2:6]([N:13]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[CH:17]=[CH:16][CH:15]=[CH:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O.CN([CH:28]=[O:29])C>>[CH2:6]([N:13]1[C:19]2[CH:20]=[CH:21][C:22]([CH:28]=[O:29])=[CH:23][C:18]=2[CH:17]=[CH:16][CH:15]=[CH:14]1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 4

HCID 962WaterHCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 12637472HCID 12637472, compound

Product 1

HCID 18998289HCID 18998289, compound

Procedure

Phosphorus oxychloride (1.9 ml, 20.4 retool) was added to DMF (10 ml) at ambient temperature and the mixture was stirred for 30 minutes under nitrogen atmosphere. To the mixture was added crude 1-benzyl-1H-1-benzazepine (3.23 g, 13.6 mmol) in DMF (5 ml) at ambient temperature. The mixture was stirred at ambient temperature for 1 hour and at 70° C. for 2 hours. Water (35 ml) was added and the mixture was stirred for 10 minutes. The mixture was extracted with EtOAc (2×100 ml) and the combined extracts were washed with H2O (2×50 ml), saturated NaHCO3 solution (50 ml) and brine (50 ml). The solution was dried over MgSO4 and concentrated in vacuo affording the title compound as a brown oil (3.42 g).

Workup

  1. stirringThe mixture was stirred at ambient temperature for 1 hour and at 70° C. for 2 hours
  2. stirringthe mixture was stirred for 10 minutes
  3. extractionThe mixture was extracted with EtOAc (2×100 ml)
  4. washthe combined extracts were washed with H2O (2×50 ml), saturated NaHCO3 solution (50 ml) and brine (50 ml)
  5. dry with materialThe solution was dried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a218d2d365cb4027a852f2784e0baafc
Source dataset
uspto-grants-1995_12
Patent number
US05478822

Reaction notes

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