Hydrochloric Acid → HCID 10757352, compound

HRID 260915Notes

Reaction equation

HRID 260915 reaction equation
[N:1]12[CH2:8][CH2:7][CH2:6][C:5]1([CH2:9][N:10]([C:13]1[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]([O:23][CH3:24])=[CH:15][CH:14]=1)[CH:11]=O)[CH2:4][CH2:3][CH2:2]2.Cl>C1COCC1>[N:1]12[CH2:8][CH2:7][CH2:6][C:5]1([CH2:9][N:10]([C:13]1[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]([O:23][CH3:24])=[CH:15][CH:14]=1)[CH3:11])[CH2:4][CH2:3][CH2:2]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 10592080HCID 10592080, compound

Product 1

HCID 10757352HCID 10757352, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 1M borane-THF complex solution (40.0 ml, 40.0 mmol), 1-[N-(1-azabicyclo[3.3.0]octan-5-yl)methyl-N-formylamino]-4-methoxynaphthalene (2.90 g, 8.95 mmol) in absolute THF (20 ml) was added dropwise at 25° C. After refluxed for 1 hour, the reaction mixture was cooled, refluxed for 10 minutes subsequent to addition of 6N-HCl (10 ml), concentrated in vacuo, made into alkaline by addition of sodium hydroxide pellets, extracted by ethyl ether, dried over anhydrous sodium sulfate, concentrated in vacuo, and purified by chromatography to afford the desired compound (2.66 g, 96.0%), as a colorless liquid.

Workup

  1. temperatureAfter refluxed for 1 hour
  2. temperaturethe reaction mixture was cooled
  3. concentrationconcentrated in vacuo
  4. additionmade into alkaline by addition of sodium hydroxide pellets
  5. extractionextracted by ethyl ether
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. custompurified by chromatography

Sources & evidence

ORD record
ord-1007a70eccd6494c87db51888799cf40
Source dataset
uspto-grants-1996_06
Patent number
US05530138

Reaction notes

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