Hydrochloric Acid → HCID 18381538, compound

HRID 2298095Notes

Reaction equation

HRID 2298095 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([CH2:22]C=O)=[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].[N:25]1([C:31](OC(C)(C)C)=O)[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl>ClCCCl.CO.O1CCOCC1.ClCCl.O>[ClH:1].[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:31][N:25]2[CH2:26][CH2:27][NH:28][CH2:29][CH2:30]2)=[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]

Participants

10

Reactant 4

HCID 313Hydrochloric AcidHCID 143452tert-Butyl piperazine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 18381537HCID 18381537, compound

Product 1

HCID 18381538HCID 18381538, compoundYield 71.1%

Reagents, catalysts & solvents 5

HCID 111,2-DichloroethaneSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-chloro-5-(2-oxoethyl)-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (0.101 g, Example 66b) in anhydrous 1,2-dichloroethane (5 ml) was added 1-piperazinecarboxylic acid, 1,1-dimethylethyl ester (0.108 g) then sodium triacetoxyborohydride (0.086 g). The reaction mixture was stirred for 14 h at room temperature. Water (10 ml) and dichloromethane (10 ml) were added and the layers were partitioned. The organic extract was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by HPLC eluting with a gradient of 0-5% ethanol in dichloromethane then by chromatography over silica gel eluting with ethyl acetate. The white powder obtained was dissolved in methanol (5 ml) and a solution of hydrochloric acid in dioxane (4N, 1 ml) was added. The mixture was stirred for 14 h at room temperature. Solvents were then removed under reduced pressure and the product obtained was triturated with diethyl ether to afford the title compound as a white powder (0.047 g).

Workup

  1. customthe layers were partitioned
  2. extractionThe organic extract
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by HPLC
  7. washeluting with a gradient of 0-5% ethanol in dichloromethane
  8. customThe white powder obtained
  9. stirringThe mixture was stirred for 14 h at room temperature
  10. customSolvents were then removed under reduced pressure
  11. customthe product obtained
  12. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-f16cff993ac0487f845145e6ec55fac4
Source dataset
uspto-grants-2002_12
Patent number
US06492355B1

Reaction notes

Loading…