Hydrochloric Acid → HCID 22622484, compound

HRID 1604395Notes

Reaction equation

HRID 1604395 reaction equation
[Br:1][C:2]1[CH:9]=[C:6]([CH:7]=O)[C:5]([OH:10])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][CH:19]1[CH2:21][CH2:20]1.[CH2:22]([NH2:25])[CH2:23]C.[BH4-].[Na+].Cl>CN(C)C=O.C(OCC)C>[CH2:22]([NH:25][CH2:7][C:6]1[CH:9]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=1[O:10][CH2:18][CH:19]1[CH2:21][CH2:20]1)[CH3:23]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 7852PropylamineHCID 11430Potassium CarbonateHCID 728635-BromosalicylaldehydeHCID 81503BromomethylcyclopropaneHCID 4311764Sodium borohydride

Product 1

HCID 22622484HCID 22622484, compoundYield 22.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To 5-bromosalicylaldehyde (15.0 g, 74 mmol) in dimethylformamide was added anhydrous potassium carbonate (36.8 g, 266 mmol) and bromomethylcyclopropane (9 ml, 93 mmol) and the solution stirred at 50° C. for 60 hours. Propylamine (26.5 g, 450 mmol) was then added and the solution left to stir at ambient temperatures for 2 hours, afterwhich diethyl ether (50 ml) and sodium borohydride (2.6 g, 68 mmol) were added and the solution left for another hour. 6 Normal hydrochloric acid (150 ml) was then added dropwise and the solution left to stir for 16 hours. Impurities were extracted with diethyl ether (200 ml×2), the solution basified with caustic liquor and the product then extracted into diethyl ether (250 ml). The organic layer was then dried over anhydrous magnesium sulphate, filtered and the solvent removed in vacuo to give the title compound (4.8 g, 22%).

Workup

  1. waitthe solution left
  2. stirringto stir at ambient temperatures for 2 hours
  3. waitthe solution left for another hour
  4. waitthe solution left
  5. stirringto stir for 16 hours
  6. extractionImpurities were extracted with diethyl ether (200 ml×2)
  7. extractionthe product then extracted into diethyl ether (250 ml)
  8. dry with materialThe organic layer was then dried over anhydrous magnesium sulphate
  9. filtrationfiltered
  10. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-dfb2ce2bea75462ca0a4864adbbac72c
Source dataset
uspto-grants-1999_11
Patent number
US05994353

Reaction notes

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