Diethyl Ether → HCID 22451492, compound

HRID 2185646Notes

Reaction equation

HRID 2185646 reaction equation
[Cl:1][C:2]1[C:3]([O:11][CH:12]2[CH2:15][N:14](C(C3C=CC=CC=3)C3C=CC=CC=3)[CH2:13]2)=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH2:6][CH2:5]2.ClC(OC(Cl)C)=O.C(OCC)C>ClCCCl>[ClH:1].[Cl:1][C:2]1[C:3]([O:11][CH:12]2[CH2:13][NH:14][CH2:15]2)=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 5213051-Chloroethyl chloroformateHCID 15390695HCID 15390695, compound

Product 1

HCID 22451492HCID 22451492, compoundYield 111.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
120 °C

Procedure

4.22 g of 3-[(5-chloro-2,3-dihydro-1H-inden-4-yl)oxy]-1-((diphenylmethyl))-azetidine were dissolved in 71 ml of 1,2-dichloroethane. 1.58 g of 1-chloroethyl chloroformate was added. The mixture was refluxed in an oil bath at 120° C. for 2.5 hours. After evaporation in vacuo the residue was refluxed in 71 ml of anhydrous methanol for 2 hours. Evaporation in vacuo gave a semi solid that was stirred with diethyl ether and filtered. The solid was recrystallized from ethanol/diethyl ether, yielding 1.57 g of 3-[(5-chloro-2,3-dihydro-1H-inden-4-yl)oxy]-azetidine hydrochloride, mp. 188° C.

Workup

  1. customAfter evaporation in vacuo the residue
  2. temperaturewas refluxed in 71 ml of anhydrous methanol for 2 hours
  3. customEvaporation in vacuo
  4. customgave a semi solid
  5. filtrationfiltered
  6. customThe solid was recrystallized from ethanol/diethyl ether

Sources & evidence

ORD record
ord-aabb80f26fdf464ab7eedbe3cc183616
Source dataset
uspto-grants-2002_06
Patent number
US06403573B1

Reaction notes

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