Chlorosuccinimide → HCID 18612494, compound

HRID 324299Notes

Reaction equation

HRID 324299 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5](=[C:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH2:12][CH2:11][N:10]3[CH:19]=[CH:20][N:21]=[C:9]23)[CH2:4][CH2:3]1.[Cl:22]N1C(=O)CCC1=O>C(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Cl:22][C:19]1[N:10]2[C:9]([C:8](=[C:5]3[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]3)[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH2:12][CH2:11]2)=[N:21][CH:20]=1

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 9838573HCID 9838573, compound

Product 1

HCID 18612494HCID 18612494, compoundYield 74.1%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 6344DichloromethaneSolvent

Procedure

6,11-Dihydro-11-(1-methyl-4-piperidinylidene)-5H-imidazo[2,1-b][3]benzazepine (28 g) was stirred in DCM (500 ml), until complete dissolution. Dibenzoyl peroxide (0.1 g) was added. N-chlorosuccinimide (13.4 g) was added portionwise and the resulting reaction mixture was stirred overnight at room temperature, then for 2 hours at reflux temperature. The solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/(CH3OH/NH3) 97/3, upgrading to 95/5). The pure fractions were collected and the solvent was evaporated. The residue was crystallized from ACN. The precipitate was filtered off and dried, yielding 23.3 g (74%) of 3-chloro-6,11-dihydro-11-(1-methyl-4-piperidinylidene)-5H-imidazo-[2,1-b][3]benzazepine (intemediate 11).

Workup

  1. customthe resulting reaction mixture
  2. temperaturefor 2 hours at reflux temperature
  3. customThe solvent was evaporated
  4. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/(CH3OH/NH3) 97/3, upgrading to 95/5)
  5. customThe pure fractions were collected
  6. customthe solvent was evaporated
  7. customThe residue was crystallized from ACN
  8. filtrationThe precipitate was filtered off
  9. customdried

Sources & evidence

ORD record
ord-acfa4d9d16974545aa0a2c3c9b3a8706
Source dataset
uspto-grants-2001_04
Patent number
US06218381B1

Reaction notes

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