Potassium Carbonate → HCID 59822300, compound

HRID 1670514Notes

Reaction equation

HRID 1670514 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[CH2:6][CH2:7][N:8](C(=O)C(F)(F)F)[CH2:9][CH2:10][C:4]=2[C:3]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20].C(=O)([O-])[O-].[K+].[K+]>C(O)C.O>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[CH2:6][CH2:7][NH:8][CH2:9][CH2:10][C:4]=2[C:3]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 59822286HCID 59822286, compound

Product 1

HCID 59822300HCID 59822300, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Slurry 7-chloro-6-(ethoxycarbonyl)-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (176 g, 503 mmol) and potassium carbonate (348 g, 2516 mmol) in ethanol (1.4 L) and water (1.4 L). Stir the mixture at room temperature for 42 h. Partition the mixture between water (2.6 L) and EtOAc (2.6 L). Collect the organic layer and back extract the aqueous layer with EtOAc (1.8 L). Wash the combined organic extracts successively with water (1.8 L) and brine (1.8 L). Collect the organic layer, dry over Na2SO4 and concentrate in vacuo to obtain the desired intermediate as a green oil (120 g, 94%).

Workup

  1. customPartition the mixture between water (2.6 L) and EtOAc (2.6 L)
  2. customCollect the organic layer
  3. extractionback extract the aqueous layer with EtOAc (1.8 L)
  4. washWash the combined organic extracts successively with water (1.8 L) and brine (1.8 L)
  5. customCollect the organic layer
  6. dry with materialdry over Na2SO4
  7. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-0b935c31ae114fd6855b6b14762ccd15
Source dataset
uspto-grants-2011_08
Patent number
US07994163B2

Reaction notes

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