Bis(2-bromoethyl) ether → HCID 59392793, compound

HRID 216710Notes

Reaction equation

HRID 216710 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([NH2:11])([CH3:10])[CH3:9])=[C:4]([CH3:12])[CH:3]=1.[CH2:13]([O:16][CH2:17][CH2:18]Br)[CH2:14]Br.C(N(CC)C(C)C)(C)C>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:11]2[CH2:18][CH2:17][O:16][CH2:13][CH2:14]2)([CH3:9])[CH3:10])=[C:4]([CH3:12])[CH:3]=1

Participants

5

Reactant 3

HCID 21521Bis(2-bromoethyl) etherHCID 81531DiisopropylethylamineHCID 593927012-(4-Bromo-2-methylphenyl)propan-2-amine

Product 1

HCID 59392793HCID 59392793, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-(4-Bromo-2-methyl-phenyl)-1-methyl-ethylamine (preparation 48, 544 mg, 2 mmol), 2,2′-dibromodiethylether (579.8 mg, 2.5 mmol) and N,N-diisopropylethylamine (1.027 ml, 6 mmol) in DMF (7 ml) is heated to 100° C. for 16 h and then allowed to cool to RT. The reaction mixture is partitioned between water and CH2Cl2. The aqueous phase is re-extracted twice, the combined organic phases are dried over Na2SO4 and concentrated in vacuo. The residue is purified by flash chromatography (silicagel, CH2Cl2: EtOAc=1:0=>0:1) to afford the title compound as a pale yellow oil, Rt=0.786 min (Acquity HPLC BEH C18, 2.1×50 mm, 1.7 micron, detection 215 nM, 0.1 min 2% CH3CN in H2O, 2% to 100% CH3CN in H2O in 1.5 min, 0.4 min 100% CH3CN+0.1% TFA, flow rate 1.0 ml/min); MS: 298 (M+1, 79Br)+.

Workup

  1. customThe reaction mixture is partitioned between water and CH2Cl2
  2. extractionThe aqueous phase is re-extracted twice
  3. dry with materialthe combined organic phases are dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by flash chromatography (silicagel, CH2Cl2: EtOAc=1:0=>0:1)

Sources & evidence

ORD record
ord-3e11856c79b047e8990c0308690f630c
Source dataset
uspto-grants-2012_06
Patent number
US08193189B2

Reaction notes

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