Hydrochloric Acid → HCID 15057234, compound

HRID 2073718Notes

Reaction equation

HRID 2073718 reaction equation
[N:1]([CH2:4][C:5]([C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1)=O)=[N+:2]=[N-:3].[CH2:17]([NH:19][CH2:20][CH3:21])[CH3:18].Cl.C([BH3-])#N.[Na+]>CO>[N:1]([CH2:4][CH:5]([C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1)[N:19]([CH2:20][CH3:21])[CH2:17][CH3:18])=[N+:2]=[N-:3]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid3×HCID 8021DiethylamineHCID 5003444Sodium cyanoborohydrideHCID 150572332-Azido-1-(naphthalen-1-yl)ethan-1-one

Product 1

HCID 15057234HCID 15057234, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

To a solution of 2.11 g (0.01 mol) of 2-azido-1-(naphthalen-1-yl)ethanone, and 3.66 g (0.05 mol) of diethylamine in 50 mL of dry methanol add 10 g of 3A molecular sieves. Adjust the pH of the mixture to pH=6 with 5N HCl in methanol and add 1 g (0.016 mol) of sodium cyanoborohydride. Follow the progress of the reaction by thin-layer chromatography on silica gel. Maintain the pH of the reaction mixture at pH=ca.6 by the addition of 5N HCl in methanol as necessary. At the completion of the reaction add concentrated hydrochloric acid until pH <2. Evaporate the solvent in vacuo. To the residue add 50 mL of water and extract with three 25 mL portions of diethyl ether. Adjust the pH of the aqueous phase to pH=11 with 4N sodium hydroxide solution and extract with three 100 mL portions of methylene chloride. Wash the combined extracts with 50 mL of water and 50 mL of saturated sodium chloride solution then dry over anhydrous sodium sulfate. Filter the drying agent and evaporate the solvent in vacuo to obtain the title compound.

Workup

  1. customthe progress of the reaction by thin-layer chromatography on silica gel
  2. temperatureMaintain the pH of the reaction mixture at pH=ca.6
  3. customEvaporate the solvent in vacuo
  4. additionTo the residue add 50 mL of water
  5. extractionextract with three 25 mL portions of diethyl ether
  6. extractionextract with three 100 mL portions of methylene chloride
  7. washWash the combined extracts with 50 mL of water and 50 mL of saturated sodium chloride solution
  8. dry with materialthen dry over anhydrous sodium sulfate
  9. filtrationFilter the drying agent
  10. customevaporate the solvent in vacuo

Sources & evidence

ORD record
ord-730ec258730f4a82910cea9af643d9d8
Source dataset
uspto-grants-1990_04
Patent number
US04920116

Reaction notes

Loading…