Allylamine → HCID 15053457, compound

HRID 1032154Notes

Reaction equation

HRID 1032154 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][CH:16]=1)[O:6][CH:7]1[CH2:10][N:9]([C:11](Cl)=[O:12])[CH2:8]1.[CH2:17]([NH2:20])[CH:18]=[CH2:19]>O1CCCC1.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][CH:16]=1)[O:6][CH:7]1[CH2:10][N:9]([C:11]([NH:20][CH2:17][CH:18]=[CH2:19])=[O:12])[CH2:8]1

Participants

5

Reactant 2

HCID 7853AllylamineHCID 19799594HCID 19799594, compound

Product 1

HCID 15053457HCID 15053457, compoundYield 76.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4.85 g (0.02 mole) of 3-(3-methoxyphenoxy)-1-azetidinecarbonyl chloride in 20 ml of tetrahydrofuran was treated with 4.5 g (0.06 mole) of 2-propenylamine and stirred for 17 hr, diluted with 200 ml of water and extracted with 3×50 ml of methylene chloride. The combined extracts were dried then concentrated in vacuo to yield 4.03 g of oil residue. The residue was chromatographed on a spinning TLC plate (chromatotron) in 3 portions (3 runs) using a ethyl acetate/methylene chloride gradient. The 4th fraction of each run was combined and concentrated in vacuo to yield a white solid (1.2 g), which was recrystallized from benzene-ligroin yielding 0.94 g (18%) of fine white crystals, m.p. 121°-123° C.

Workup

  1. extractionextracted with 3×50 ml of methylene chloride
  2. customThe combined extracts were dried
  3. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-695a23ff44f04f73a709ce8aa6c24321
Source dataset
uspto-grants-1990_09
Patent number
US04956359

Reaction notes

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