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

HRID 469312Notes

Reaction equation

HRID 469312 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 (6.00 mmol) N-chlorosuccinimide were added to 1.23 g (5.00 mmol) 3-piperidin-4-yl-1,3,4,5-tetrahydro-benzo[d][1,3]diazepin-2-one in 10.0 mL carbon tetrachloride and the mixture was refluxed for 72 h. The solvent was eliminated i. vac. and the crude product was purified by flash chromatography. The fractions containing the product were concentrated by rotary evaporation and purified by preparative HPLC.

Workup

  1. temperaturethe mixture was refluxed for 72 h
  2. customand the crude product was purified by flash chromatography
  3. additionThe fractions containing the product
  4. concentrationwere concentrated by rotary evaporation
  5. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-71a4b30b152d47328eb7e0aa00acabf9
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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