Allylamine → HCID 15053431, compound

HRID 2081410Notes

Reaction equation

HRID 2081410 reaction equation
Cl[C:2]([N:4]1[CH2:7][CH:6]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=2)[CH2:5]1)=[O:3].[CH2:16]([NH2:19])[CH:17]=[CH2:18]>O1CCCC1>[Cl:15][C:11]1[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=1)[O:8][CH:6]1[CH2:7][N:4]([C:2]([NH:19][CH2:16][CH:17]=[CH2:18])=[O:3])[CH2:5]1

Participants

4

Reactant 2

HCID 7853AllylamineHCID 15042230HCID 15042230, compound

Product 1

HCID 15053431HCID 15053431, compoundYield 37.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5.4 g (0.017 mole) of 1-chlorocarbonyl-3-(3-chlorophenoxy)azetidine in 20 ml of tetrahydrofuran was treated with 2.3 g (0.04 mole) of 2-propenylamine and stirred for 2 hr. The reaction solution was concentrated in vacuo to a rose beige solid. Trituration of the solid with water gave, after filtering, 4.4 g of crude product. After drying, the solid was recrystallized with charcoal treatment from 2% acetone/isopropyl ether to yield 1.7 g (37.5%) of pale beige crystals, m.p. 87°-89° C.

Workup

  1. concentrationThe reaction solution was concentrated in vacuo to a rose beige solid
  2. customTrituration of the solid with water gave
  3. filtrationafter filtering
  4. customAfter drying
  5. customthe solid was recrystallized with charcoal treatment from 2% acetone/isopropyl ether

Sources & evidence

ORD record
ord-859c9dd92b7d4a1c896a6be0528e2b27
Source dataset
uspto-grants-1993_02
Patent number
US05183902

Reaction notes

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