Dimethylamine → 2-bromo-N,N-dimethylbenzylamine

HRID 1107724

Reaction equation

HRID 1107724 reaction equation
[CH3:1][NH:2][CH3:3].[Br:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH2:7]Br>CO>[Br:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH2:7][N:2]([CH3:3])[CH3:1]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 769652-Bromobenzyl bromide

Product 1

HCID 747922-bromo-N,N-dimethylbenzylamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dimethylamine (33% w/w in methanol) (25 ml) was added to 2-bromobenzylbromide (7.5 g 30 mmol) at 0° C. in methanol (35 ml), and the solution stirred for 30 min., evaporated, diluted with water and extracted twice with diethyl ether. The combined extracts were dried over sodium sulphate and evaporated to give product as a yellow oil (6.0 g). M+ 215/213; 360 MHz 1H n.m.r (CDCl3) 7.54 (1H, dd, J 1.2, 8.0 Hz), 7.42 (1H, dd, J 1.6, 7.6 Hz), 7.30-7.26 (1H, m), 7.11 (1H, dt, J 1.7, 7.7 Hz), 3.52 (2H, s), 2.30 (6H, s).

Workup

  1. customevaporated
  2. additiondiluted with water
  3. extractionextracted twice with diethyl ether
  4. dry with materialThe combined extracts were dried over sodium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-df42aafd75f442d2b8d83ab3dd190459
Source dataset
uspto-grants-2000_05
Patent number
US06063789

Linked notes

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