Benzyl-(1-amino-3-chloro-2-propanol) → 1-benzylazetidin-3-ol

HRID 980770Notes

Reaction equation

HRID 980770 reaction equation
[CH2:1]([NH:8][CH2:9][CH:10]([OH:13])[CH2:11]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(N(CC)CC)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:1]([N:8]1[CH2:11][CH:10]([OH:13])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 173441Benzyl-(1-amino-3-chloro-2-propanol)

Product 1

HCID 38013451-benzylazetidin-3-olYield 92.6%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8471TriethylamineSolvent

Procedure

333 g of N-benzyl-3-amino-1-chloropropan-2-ol was taken up in 1665 ml of triethylamine and 10 g of tetrabutylammonium iodide was added. The resulting mixture was stirred under reflux for 13 hours, after which it was cooled, the hydrochloride precipitate filtered off and the filtrate washed twice with triethylamine. The combined filtrates were evaporated to yield 252 g of an oil, which was crystallized from 250 ml of toluene and 50 ml of hexane to yield 180.8 g of l as white crystals, m.p.: 66°-67° C., being a yield (based on amino-propanol) of 66.5% .

Workup

  1. temperatureunder reflux for 13 hours
  2. temperatureafter which it was cooled
  3. filtrationthe hydrochloride precipitate filtered off
  4. washthe filtrate washed twice with triethylamine
  5. customThe combined filtrates were evaporated

Sources & evidence

ORD record
ord-c331295165e6462bab5721d677449ccd
Source dataset
uspto-grants-1987_01
Patent number
US04639334

Reaction notes

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