Potassium Carbonate → 2-[4-(1-Phenyl-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-butyl]-isoindol-1,3-dione

HRID 2251937Notes

Reaction equation

HRID 2251937 reaction equation
[C:1]1([CH:7]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[CH2:11][CH2:10][NH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:19][CH2:20][CH2:21][CH2:22][N:23]1[C:27](=[O:28])[C:26]2=[CH:29][CH:30]=[CH:31][CH:32]=[C:25]2[C:24]1=[O:33].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:1]1([CH:7]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[CH2:11][CH2:10][N:9]([CH2:19][CH2:20][CH2:21][CH2:22][N:23]3[C:27](=[O:28])[C:26]4[C:25](=[CH:32][CH:31]=[CH:30][CH:29]=4)[C:24]3=[O:33])[CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 93575N-(4-Bromobutyl)phthalimideHCID 2870943HCID 2870943, compound

Product 1

HCID 541071242-[4-(1-Phenyl-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-butyl]-isoindol-1,3-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

20.0 g (89.5 mmol) 1-phenyl-1,2,4,5-tetrahydrobenzo[d]azepine, 25.2 g (89.5 mmol) N-(4-bromobutyl)-phthalimide and 18.5 g (134.3 mmol) potassium carbonate are stirred in 200 ml DMF for 6 hours at 60° C. The mixture is concentrated under vacuum and the residue is distributed between 300 ml acetic acid ethyl ester and 100 ml water. The watery phase is extracted with 50 ml acetic acid ethyl ester and the combined organic phases are washed with water. The organic phase is dried over sodium sulfate and evaporated under vacuum until dried: Yield 39.5 g.

Workup

  1. concentrationThe mixture is concentrated under vacuum
  2. extractionThe watery phase is extracted with 50 ml acetic acid ethyl ester
  3. washthe combined organic phases are washed with water
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. customevaporated under vacuum
  6. customuntil dried

Sources & evidence

ORD record
ord-19a1bf9be7004968a21bf9739991ae41
Source dataset
uspto-grants-2008_01
Patent number
US07320993B1

Reaction notes

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