Triethylamine → HCID 18540800, compound

HRID 411283Notes

Reaction equation

HRID 411283 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].C(N(CC)CC)C.[Br:22][CH2:23][C:24](Br)=[O:25]>ClCCl>[CH2:3]([N:2]([CH3:1])[C:24](=[O:25])[CH2:23][Br:22])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61147Bromoacetyl bromideHCID 81746N-Methyl-1-dodecanamine

Product 1

HCID 18540800HCID 18540800, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N-methyl-N-dodecylamine (2.5 ml) and triethylamine (1.4 ml) in dichloromethane (10 ml) was added with stirring and ice cooling a solution of bromoacetyl bromide (0.87 ml) in dichloromethane (10 ml). The cooling bath was removed after 30 min and the reaction stood for 16 h at ambient temperature. The mixture was washed with water and saturated sodium hydrogen carbonate, dried (K2CO3) and the solution purified by flash chromatography (silica, methanol-dichloromethane). Appropriate fractions were combined and evaporated to a pale yellow oil, yield 1.53 g (48%). 1H-NMR (CDCl3) δ0.8 (3H,t), 1.2 (18H,m), 1.5 (2H,m,), 2.88 and 2.99 (3H,2xs), 3.27 (2H,m), 3.77 and 3.79 (2H,s)); MS (APCI+) found (M+1)=320, 322, C15H30BrNO requires 319,321.

Workup

  1. customThe cooling bath was removed after 30 min
  2. washThe mixture was washed with water and saturated sodium hydrogen carbonate
  3. dry with materialdried (K2CO3)
  4. customthe solution purified by flash chromatography (silica, methanol-dichloromethane)
  5. customevaporated to a pale yellow oil, yield 1.53 g (48%)

Sources & evidence

ORD record
ord-f7f0ca007d93439db5c633f557ae97e2
Source dataset
uspto-grants-2003_05
Patent number
US06559155B1

Reaction notes

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