Benzylamine → HCID 15933784, compound

HRID 366872Notes

Reaction equation

HRID 366872 reaction equation
[CH3:1]/[C:2](=[CH:5]\[CH2:6]O)/[CH2:3]O.C(N(CC)CC)C.CS(Cl)(=O)=O.[CH2:20]([NH2:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(OCC)(=O)C>[CH2:20]([N:27]1[CH2:6][CH:5]=[C:2]([CH3:3])[CH2:1]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 7504BenzylamineHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 12778450HCID 12778450, compound

Product 1

HCID 15933784HCID 15933784, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
5 °C

Procedure

To a solution containing 40.8 g (0.4 mol) of E-2-methyl-2-butene-1,4-diol, 83.8 g (0.8 mol) of triethylamine, and 416.6 g of ethyl acetate in a round flask reactor, methanesulfonyl chloride was added dropwise with stirring for 30 min. at about 5° C. using an ice-bath. After addition, the mixture was allowed to react with stirring for 2 hours at room temperature. To the mixture, 171.7 g (1.6 mol) of benzylamine was added continuously dropwise with stirring for 30 min. at ambient temperature. After 2 hours of stirring, the crystallized solid was removed by filtration; 42.0 g of 35% HCl (aq) was added to the filtrate, and then excess benzylamine hydrochloride was removed by filtration or extraction. After the solvent was evaporated under reduced pressure, 54.2 g of 1-benzyl-3-methyl-3-pyrroline (yield 78.2%) was obtained.

Workup

  1. additionAfter addition
  2. customto react
  3. stirringwith stirring for 2 hours at room temperature
  4. stirringwith stirring for 30 min. at ambient temperature
  5. stirringAfter 2 hours of stirring
  6. customthe crystallized solid was removed by filtration
  7. addition42.0 g of 35% HCl (aq) was added to the filtrate
  8. customexcess benzylamine hydrochloride was removed by filtration or extraction
  9. customAfter the solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-f7b25bc934bb4addab875d6eb86acb64
Source dataset
uspto-grants-2000_10
Patent number
US06130338

Reaction notes

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