Bis(2-chloroethyl)amine hydrochloride → Eltoprazine

HRID 726542Notes

Reaction equation

HRID 726542 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([NH2:11])[C:5]=2[O:4][CH2:3][CH2:2]1.Cl.Cl[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]Cl>ClC1C=CC=CC=1>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([N:11]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[C:5]=2[O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 522769Bis(2-chloroethyl)amine hydrochlorideHCID 117883872,3-Dihydro-1,4-benzodioxin-5-amine

Product 1

HCID 65853EltoprazineYield 90.8%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A solution of the product of Example 2 (1.50 g, 0.010 mol) and bis(2-chloroethyl)amine hydrochloride (1.77 g 0.01 mol) in chlorobenzene (20 ml) was heated under reflux for 24 h, cooled to room temperature and evaporated in vacuo. The white solid was dissolved in aqueous sodium hydroxide (100 ml) and extracted into ethyl acetate (3×50 ml). The extracts were dried (MgSO4) and evaporated in vacuo to give the product (2.00 g).

Workup

  1. temperatureunder reflux for 24 h
  2. customevaporated in vacuo
  3. dissolutionThe white solid was dissolved in aqueous sodium hydroxide (100 ml)
  4. extractionextracted into ethyl acetate (3×50 ml)
  5. dry with materialThe extracts were dried (MgSO4)
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-97f7d1a3249c4761afcd17bcc44ac90d
Source dataset
uspto-grants-1998_01
Patent number
US05710149

Reaction notes

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