Cyclooctanecarbaldehyde → N-[1-(cyclooctylmethyl)piperidin-4-yl]xanthene-9-carboxamide

HRID 370269Notes

Reaction equation

HRID 370269 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:9]([CH:11]2[C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[O:18][C:17]3[C:12]2=[CH:13][CH:14]=[CH:15][CH:16]=3)=[O:10])[CH2:4][CH2:3]1.[CH:25]1([CH:33]=O)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>O1CCCC1>[CH:25]1([CH2:33][N:2]2[CH2:3][CH2:4][CH:5]([NH:8][C:9]([CH:11]3[C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=4[O:18][C:19]4[C:24]3=[CH:23][CH:22]=[CH:21][CH:20]=4)=[O:10])[CH2:6][CH2:7]2)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

6

Reactant 4

HCID 81190CyclooctanecarbaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 23283003N-(piperidin-4-yl)xanthene-9-carboxamide hydrochloride

Product 1

HCID 10765199N-[1-(cyclooctylmethyl)piperidin-4-yl]xanthene-9-carboxamideYield 45.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.16 g of N-(piperidin-4-yl)xanthene-9-carboxamide hydrochloride and 586 mg of cyclooctanecarbaldehyde were suspended in 60 ml of tetrahydrofuran at room temperature, and 1.60 g of sodium triacetoxyborohydride was added thereto, followed by stirring for 12 hours at the same temperature. Saturated aqueous sodium bicarbonate was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, followed by drying over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, the obtained residue was purified by silica gel column chromatography (developing solvent: chloroform--chloroform/methanol=50/1), and 660 mg of the title compound as a white solid was obtained.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium chloride
  3. dry with materialby drying over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography (developing solvent: chloroform--chloroform/methanol=50/1)

Sources & evidence

ORD record
ord-9d8f9799d59b4fccaab715570a02b422
Source dataset
uspto-grants-2000_10
Patent number
US06140338

Reaction notes

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