Bis(2-chloroethyl)amine hydrochloride → Eltoprazine

HRID 1952742Notes

Reaction equation

HRID 1952742 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 65853Eltoprazine

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A stirred mixture of 1,4-benzodioxan-5-amine (21.6 g; prepared by basification of the above hydrochloride salt), bis(2-chloroethyl)amine monohydrochloride (25 g) and chlorobenzene (250 ml) was heated under reflux for 72 hours, then the solvent was removed in vacuo. The residue was diluted with water (250 ml), basified by the addition of 5M aqueous sodium hydroxide solution, and the product was extracted into ethyl acetate (5×100 ml). The extracts were dried (MgSO4), and the solvent removed in vacuo to give 1-(1,4-benzodioxan-5-yl)piperazine as a brown oil (29.2 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 72 hours
  3. customthe solvent was removed in vacuo
  4. additionThe residue was diluted with water (250 ml)
  5. additionbasified by the addition of 5M aqueous sodium hydroxide solution
  6. extractionthe product was extracted into ethyl acetate (5×100 ml)
  7. dry with materialThe extracts were dried (MgSO4)
  8. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-2b25a809700c4a3a945dd6805a46ac7f
Source dataset
uspto-grants-2000_09
Patent number
US06114334

Reaction notes

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