Allylamine → HCID 15053455, compound

HRID 2081462Notes

Reaction equation

HRID 2081462 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[O:5][CH:6]1[CH2:9][N:8]([C:10](Cl)=[O:11])[CH2:7]1.[CH2:16]([NH2:19])[CH:17]=[CH2:18]>O1CCCC1.O>[CH3:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[O:5][CH:6]1[CH2:9][N:8]([C:10]([NH:19][CH2:16][CH:17]=[CH2:18])=[O:11])[CH2:7]1

Participants

5

Reactant 2

HCID 7853AllylamineHCID 19799586HCID 19799586, compound

Product 1

HCID 15053455HCID 15053455, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 3.92 g (0.01 mole) of crude (57.59%) 3-(3-methylphenoxy)-1-azetidinecarbonyl chloride in 15 ml of tetrahydrofuran was treated with 2.25 g (0.03 mole) of 2-propenylamine. After stirring for 18 hr, the reaction mixture was diluted with 200 ml of water and a reddish oil separated. A sample of this oil crystallized at -70° C. and was used to seed the oil residue. The resulting solid was collected by filtration to yield 3.6 g which was recrystallized from benzene-ligroin yielding, after charcoal treatment, 1.53 g (62.2%) of pale beige crystals, m.p. 95°-96° C.

Workup

  1. customa reddish oil separated
  2. customA sample of this oil crystallized at -70° C.
  3. filtrationThe resulting solid was collected by filtration
  4. customto yield 3.6 g which
  5. customwas recrystallized from benzene-ligroin yielding

Sources & evidence

ORD record
ord-22c5243df7cd413292e2b02d31a47480
Source dataset
uspto-grants-1993_02
Patent number
US05183902

Reaction notes

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