Cycloheptylamine → HCID 53861143, compound

HRID 1281706Notes

Reaction equation

HRID 1281706 reaction equation
Cl[C:2]1[N:6]([C@H:7]2[O:15][CH2:14][C@@H:12]([OH:13])[C@H:10]([OH:11])[C@@H:8]2[OH:9])[C:5]2[CH:16]=[C:17]([Cl:21])[C:18]([Cl:20])=[CH:19][C:4]=2[N:3]=1.[CH:22]1([NH2:29])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>C(O)C>[CH:22]1([NH:29][C:2]2[N:6]([C@H:7]3[O:15][CH2:14][C@@H:12]([OH:13])[C@H:10]([OH:11])[C@@H:8]3[OH:9])[C:5]3[CH:16]=[C:17]([Cl:21])[C:18]([Cl:20])=[CH:19][C:4]=3[N:3]=2)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

4

Reactant 2

HCID 2899CycloheptylamineHCID 54088501HCID 54088501, compound

Product 1

HCID 53861143HCID 53861143, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Compound 4 (200 mg, 0.57 mmol) was dissolved in ethanol (4 mL). Cycloheptylamine (3.9 mL, 28 mmol) was added, the flask was sealed and the reaction mixture stirred at 60 ûC. for 2 days. The mixture was decanted and evaporated to dryness at 65 ûC. under high vacuum. The residue was dissolved in ethyl acetate (20 mL), and crystals of cycloheptylammonium chloride were removed by filtration. The organic extract was dried over sodium sulfate, filtered and the filtrate was evaporated under reduced pressure. The residue was subjected to silica gel chromatography [2×15 cm, eluent:gradient of methanol (0-6%) in dichloromethane]. Fractions that contained the major spot [Rf (system 3): 0.30] were evaporated and the resulting solid was suspended in boiling dichloromethane. Methanol was added until complete dissolution of the solid. Compound 7 crystallized from this solution (150 mg, 61%).

Workup

  1. customthe flask was sealed
  2. customThe mixture was decanted
  3. customevaporated to dryness at 65 ûC
  4. dissolutionThe residue was dissolved in ethyl acetate (20 mL)
  5. customcrystals of cycloheptylammonium chloride were removed by filtration
  6. extractionThe organic extract
  7. dry with materialwas dried over sodium sulfate
  8. filtrationfiltered
  9. customthe filtrate was evaporated under reduced pressure
  10. customwere evaporated
  11. additionMethanol was added until complete dissolution of the solid
  12. customCompound 7 crystallized from this solution (150 mg, 61%)

Sources & evidence

ORD record
ord-cb978ec78b4b4b59a39f5292d6346dc7
Source dataset
uspto-grants-2002_09
Patent number
US06455507B1

Reaction notes

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