Allylamine → HCID 15053450, compound

HRID 2081457Notes

Reaction equation

HRID 2081457 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][CH:7]2[CH2:10][N:9]([C:11](Cl)=[O:12])[CH2:8]2)=[CH:4][CH:3]=1.[CH2:16]([NH2:19])[CH:17]=[CH2:18]>O1CCCC1.O>[Br:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][CH:7]2[CH2:10][N:9]([C:11]([NH:19][CH2:16][CH:17]=[CH2:18])=[O:12])[CH2:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 7853AllylamineHCID 15053366HCID 15053366, compound

Product 1

HCID 15053450HCID 15053450, compoundYield 59.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 5.8 g (0.02 mole) of 3-(4-bromophenoxy)-1-azetidinecarbonyl chloride in 20 ml of tetrahydrofuran was treated with 4.5 g (0.06 mole) of 2-propenylamine and stirring continued for 18 hr. The reaction mixture was diluted with 200 ml of water and the oil which separated slowly solidified. After collecting the solid by filtration, it was triturated 4 times with boiling isopropyl ether. The combined triturates upon cooling yielded 3.7 g (59.5%) of white crystals, m.p. 100°-101° C.

Workup

  1. customthe oil which separated slowly solidified
  2. customAfter collecting the solid
  3. filtrationby filtration, it
  4. customwas triturated 4 times with boiling isopropyl ether
  5. temperatureThe combined triturates upon cooling

Sources & evidence

ORD record
ord-35cd63b2f1454d8d890b3c9b9c97e5e2
Source dataset
uspto-grants-1993_02
Patent number
US05183902

Reaction notes

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