Ammonium Chloride → HCID 131723678, compound

HRID 2298039Notes

Reaction equation

HRID 2298039 reaction equation
[N+:1]([C:4]1[CH:23]=[CH:22][CH:21]=[CH:20][C:5]=1[C:6]([NH:8][CH2:9][C:10]12[CH2:19][CH:14]3[CH2:15][CH:16]([CH2:18][CH:12]([CH2:13]3)[CH2:11]1)[CH2:17]2)=[O:7])([O-])=O.[Cl-:24].[NH4+:25]>[Fe].C(O)C.O>[ClH:24].[ClH:24].[NH2:1][C:4]1[C:23]([N:25]2[CH2:10][CH2:9][NH:8][CH2:6][CH2:5]2)=[CH:22][CH:21]=[CH:20][C:5]=1[C:6]([NH:8][CH2:9][C:10]12[CH2:19][CH:14]3[CH2:15][CH:16]([CH2:18][CH:12]([CH2:13]3)[CH2:11]1)[CH2:17]2)=[O:7]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 8923892HCID 8923892, compound

Product 1

HCID 131723678HCID 131723678, compoundYield 85.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

A suspension of 3-(4-{1,1-dimethylethyl}oxycarbonyl]-piperazin-1-yl)-2-nitro-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (3.8 g, Example 1b), iron powder (2.13 g) and ammonium chloride (2.04 g) in 2:1 ethanol/water (90 ml) was heated at reflux, under a nitrogen atmosphere, for 2 h. The cooled reaction mixture was filtered and the filtrate partitioned between water and ethyl acetate. The organic layer was separated and washed with water twice further, dried over magnesium sulfate, filtered and the filtrate concentrated under reduced pressure to give a residue. Purification of the residue by chromatography over silica gel, eluting with 20% ethyl acetate in iso-hexane, yielded the subtitle compound as a solid (2.27 g).

Workup

  1. temperaturewas heated
  2. temperatureat reflux, under a nitrogen atmosphere, for 2 h
  3. customThe cooled reaction mixture
  4. filtrationwas filtered
  5. customthe filtrate partitioned between water and ethyl acetate
  6. customThe organic layer was separated
  7. washwashed with water twice further
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationthe filtrate concentrated under reduced pressure
  11. customto give a residue
  12. customPurification of the residue by chromatography over silica gel
  13. washeluting with 20% ethyl acetate in iso-hexane

Sources & evidence

ORD record
ord-5bed8401eb2d46758443481ec7e0101b
Source dataset
uspto-grants-2002_12
Patent number
US06492355B1

Reaction notes

Loading…