Bis(2-chloroethyl)amine hydrochloride → Eltoprazine

HRID 1750149Notes

Reaction equation

HRID 1750149 reaction equation
Cl.Cl[CH2:3][CH2:4][NH:5][CH2:6][CH2:7]Cl.[O:9]1[CH2:14][CH2:13][O:12][C:11]2[C:15]([NH2:19])=[CH:16][CH:17]=[CH:18][C:10]1=2>ClC1C=CC=CC=1>[O:9]1[CH2:14][CH2:13][O:12][C:11]2[C:15]([N:19]3[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]3)=[CH:16][CH:17]=[CH:18][C:10]1=2

Participants

4

Reactant 2

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

Product 1

HCID 65853EltoprazineYield 51%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

Bis(2-chloroethyl)amine hydrochloride salt (452 mg, 2.54 mmol) was added to a solution of intermediate 60 (320 mg, 2.12 mmol) in chlorobenzene (4 mL) and the mixture was heated to reflux and stirred overnight. The solvent was removed under reduced pressure and the residue was purified by flash chromatography on silica gel column (DCM:MeOH=30:1-20:1), followed by a wash with EtOAc, to give 1-(2,3-dihydrobenzo[b][1,4]dioxin-5-yl)piperazine (intermediate 61) (236 mg, 51%). HPLC: 99%, RT 1.673 min. MS (ESI) m/z 221.1 [M+H]+.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was purified by flash chromatography on silica gel column (DCM:MeOH=30:1-20:1)
  5. washa wash with EtOAc

Sources & evidence

ORD record
ord-39fe051a1f544c9eb28782e2a30bb9d1
Source dataset
uspto-grants-2015_10
Patent number
US09156822B2

Reaction notes

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