Chlorosuccinimide → 7-Chloro-3-piperidin-4-yl-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one

HRID 74491Notes

Reaction equation

HRID 74491 reaction equation
[Cl:1]N1C(=O)CCC1=O.[NH:9]1[CH2:14][CH2:13][CH:12]([N:15]2[CH2:21][CH2:20][C:19]3[CH:22]=[CH:23][CH:24]=[CH:25][C:18]=3[NH:17][C:16]2=[O:26])[CH2:11][CH2:10]1>C(Cl)(Cl)(Cl)Cl>[Cl:1][C:23]1[CH:24]=[CH:25][C:18]2[NH:17][C:16](=[O:26])[N:15]([CH:12]3[CH2:11][CH2:10][NH:9][CH2:14][CH2:13]3)[CH2:21][CH2:20][C:19]=2[CH:22]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 113795873-(Piperidin-4-yl)-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-one

Product 1

HCID 581811547-Chloro-3-piperidin-4-yl-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

801 mg (6.0 mmol) N-chlorosuccinimide were added to 1.23 g (5.0 mmol) 3-piperidin-4-yl-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one in 10 mL carbon tetrachloride and the reaction mixture was refluxed for 3 days. The solvent was evaporated down using the rotary evaporator and the residue was purified by flash chromatography. The product fractions were combined and the solvent was eliminated using the rotary evaporator. For further purification the product fractions were purified by preparative HPLC. The product fractions were combined and evaporated to dryness using the rotary evaporator.

Workup

  1. temperaturethe reaction mixture was refluxed for 3 days
  2. customThe solvent was evaporated down
  3. customthe rotary evaporator
  4. customthe residue was purified by flash chromatography
  5. customthe rotary evaporator
  6. customFor further purification the product fractions
  7. customwere purified by preparative HPLC
  8. customevaporated to dryness
  9. customthe rotary evaporator

Sources & evidence

ORD record
ord-bb48cb87e0fe4ab7920c78ae22c3ec23
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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