Diethylamine → (p-bromobenzyl)diethyl amine

HRID 1505914Notes

Reaction equation

HRID 1505914 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][CH:3]=1.[CH2:10]([N:12](CC)[CH2:13][CH3:14])[CH3:11].C(NCC)C>C1COCC1>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:12]([CH2:13][CH3:14])[CH2:10][CH3:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 8471TriethylamineHCID 685274-Bromobenzyl bromide

Product 1

HCID 10999178(p-bromobenzyl)diethyl amineYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-bromobenzyl bromide (1.0 g, 4.0 mmol), triethylamine (0.84 mL, 6.0 mmol) and diethylamine (0.84 mL, 8.0 mmol) in THF (20 mL) was stirred at ambient temperature for 16 h. The solvent was evaporated and the resultant residue diluted with saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate (2×50 mL). The combined organic layer was dried over sodium sulfate, filtered and evaporated to afford the title compound (0.85 g, 88%). 1H NMR (CDCl3, 300 MHz): 7.45-7.38 (m, 2H), 7.27-7.18 (m, 2H), 3.50 (s, 2H), 2.50 (q, J=7.1 Hz, 4H), 1.03 (t, J=7.1 Hz, 6H). LCMS (Method G): RT=1.98 min, M−H+=242.

Workup

  1. customThe solvent was evaporated
  2. additionthe resultant residue diluted with saturated aqueous sodium bicarbonate solution
  3. extractionextracted with ethyl acetate (2×50 mL)
  4. dry with materialThe combined organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-a21aedb22d044998bdd621f4f96d5bfe
Source dataset
uspto-grants-2015_12
Patent number
US09216980B2

Reaction notes

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