Acetonitrile → 5-Aziridin-1-yl-2-chloro-N-(tricyclo[3.3.1.13,7]dec-1-yhnethyl)-benzamide

HRID 1532324Notes

Reaction equation

HRID 1532324 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([NH:22][CH2:23][CH2:24]Cl)=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:5].C(=O)([O-])[O-].[Cs+].[Cs+].C(#N)C>O>[N:22]1([C:19]2[CH:20]=[CH:21][C:2]([Cl:1])=[C:3]([CH:18]=2)[C:4]([NH:6][CH2:7][C:8]23[CH2:17][CH:12]4[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]4)[CH2:9]2)[CH2:15]3)=[O:5])[CH2:23][CH2:24]1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 10796Cesium carbonateHCID 114176532-Chloro-5-(2-chloroethyl)amino-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)benzamide

Product 1

HCID 206700525-Aziridin-1-yl-2-chloro-N-(tricyclo[3.3.1.13,7]dec-1-yhnethyl)-benzamideYield 17%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

2-Chloro-5-(2-chloroethyl)amino-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (0.15 g), cesium carbonate (0.192 g) and acetonitrile (3 ml) were combined and heated in a sealed tube at 100° C. for 24 hours. The cooled reaction mixture was poured into water (50 ml) and the product extracted into ethyl acetate, dried over magnesium sulphate, filtered and concentrated under reduced pressure. The crude product was purified by NPHPLC eluting with 0-5% ethanol in dichloromethane to give the title compound as a white solid (0.023 g).

Workup

  1. customThe cooled reaction mixture
  2. extractionthe product extracted into ethyl acetate
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by NPHPLC
  7. washeluting with 0-5% ethanol in dichloromethane

Sources & evidence

ORD record
ord-6edbd64372434046b8f795b328408452
Source dataset
uspto-grants-2001_03
Patent number
US06201024B1

Reaction notes

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