Hydrochloric Acid → HCID 54116400, compound

HRID 2259439Notes

Reaction equation

HRID 2259439 reaction equation
[CH2:1]([NH2:4])[CH:2]=[CH2:3].S([O-])([O-])(=O)=O.[Na+].[Na+].[Cl:12][C:13]1[CH:14]=[C:15]([CH:20]=[C:21]([Cl:23])[CH:22]=1)[CH:16]=[CH:17][CH:18]=O.[BH4-].[Na+].Cl>C(Cl)Cl>[CH2:1]([NH:4][CH2:18][CH:17]=[CH:16][C:15]1[CH:20]=[C:21]([Cl:23])[CH:22]=[C:13]([Cl:12])[CH:14]=1)[CH:2]=[CH2:3]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7853AllylamineHCID 24436Sodium SulfateHCID 4311764Sodium borohydrideHCID 53948974HCID 53948974, compound

Product 1

HCID 54116400HCID 54116400, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.5 ml (60 mmol, 3.4 g) of allylamine and 17.0 g of sodium sulfate were added to 12.0 g (59.7 mmol) of 3,5-dichlorocinnamaldehyde in 180 ml of methylene chloride, and the mixture was stirred at room temperature for 24 h. The sodium sulfate was then filtered and washed with methylene chloride, and the filtrate was evaporated to dryness. The resulting yellow oil was dissolved in 200 ml of absolute methanol and, under nitrogen, 2.5 g (66.0 mmol) of sodium borohydride were added in portions. The temperature of the mixture rose slightly and it was then stirred for 1 h and subsequently neutralized (pH=7) with 10% strength hydrochloric acid. The solvent was removed under reduced pressure, and the residue was taken up in methylene chloride. The organic phase was washed twice with water, dried over sodium sulfate and concentrated. The residue was purified by column chromatography (silica gel, methylene chloride +5% methanol). Yield: 9.2 g (63%) of yellow oil.

Workup

  1. filtrationThe sodium sulfate was then filtered
  2. washwashed with methylene chloride
  3. customthe filtrate was evaporated to dryness
  4. dissolutionThe resulting yellow oil was dissolved in 200 ml of absolute methanol and, under nitrogen
  5. stirringit was then stirred for 1 h
  6. customThe solvent was removed under reduced pressure
  7. washThe organic phase was washed twice with water
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated
  10. customThe residue was purified by column chromatography (silica gel, methylene chloride +5% methanol)

Sources & evidence

ORD record
ord-8bed60040a214930b760f1e6505dbf76
Source dataset
uspto-grants-1995_12
Patent number
US05473080

Reaction notes

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