4-Bromobenzyl bromide → HCID 61517831, compound

HRID 2101207Notes

Reaction equation

HRID 2101207 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][CH:3]=1.[CH2:10]([O:12][CH2:13][CH2:14][NH:15][CH2:16][CH3:17])C>CN(C=O)C>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:15]([CH2:14][CH2:13][O:12][CH3:10])[CH2:16][CH3:17])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 685274-Bromobenzyl bromideHCID 520890(2-ETHOXY-ETHYL)-ETHYL-AMINE

Product 1

HCID 61517831HCID 61517831, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Bromobenzylbromide (4.01 g) was added to a solution of N-(2-ethoxyethyl)ethanamine (3.64 g) in DMF (40 ml). After stirring at ambient temperature for 18 h, the mixture was partitioned between diethyl ether and water. The organic phase was extracted with 2N aqueous hydrochloric acid which was then taken to pH 10 by addition of 2N sodium hydroxide solution. This was then extracted with diethyl ether which was dried and the solvent removed under vacuum to yield the title compound as a yellow oil (4.25 g). 1H NMR (DMSO-D6) 0.95 (t, 2H), 2.45 (q, 3H), 2.55 (t, 2H), 3.2 (s, 3H), 3.36 (t, 2H), 3.52 (s, 2H), 7.24 (d, 2H), 7.46 (d, 2H).

Workup

  1. customthe mixture was partitioned between diethyl ether and water
  2. extractionThe organic phase was extracted with 2N aqueous hydrochloric acid which
  3. additionwas then taken to pH 10 by addition of 2N sodium hydroxide solution
  4. extractionThis was then extracted with diethyl ether which
  5. customwas dried
  6. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-f947c46f00b34de28672a048ca3072cc
Source dataset
uspto-grants-2009_08
Patent number
US07572826B2

Reaction notes

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