Triethylamine → HCID 68872277, compound

HRID 2112038Notes

Reaction equation

HRID 2112038 reaction equation
[CH2:1]([NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C(N(CC)CC)C.[Br:22][CH2:23][C:24](Cl)=[O:25]>C(Cl)Cl>[CH2:8]([N:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[C:24](=[O:25])[CH2:23][Br:22])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 89602Bromoacetyl chlorideHCID 485395Benzenemethanamine, N-hexyl-

Product 1

HCID 68872277HCID 68872277, compoundYield 58.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-hexylbenzylamine (4.2 g, 21.953 mmol) and triethylamine (3.98 ml, 28.539 mmol) were mixed in DCM (20 ml) and cooled in an ice-bath. Bromacetyl chloride (3.455 mg, 21.953 mmol) in DCM (5 ml) was added. The mixture was stirred over weekend and the temperature was allowed going up to room temperature. The mixture was washed with water mixed with 1% hydrochloric acid (water phase pH˜4-5) and brine, dried with magnesium sulphate, and evaporated. Column chromatography of the residue on silica gel using ethyl acetate/heptane (10:90, then 20:80) as eluant gave 4.0 g desired product, yield 58%.

Workup

  1. temperaturecooled in an ice-bath
  2. customwas allowed going up to room temperature
  3. washThe mixture was washed with water
  4. additionmixed with 1% hydrochloric acid (water phase pH˜4-5) and brine
  5. dry with materialdried with magnesium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-4a770f917d7d410eaca8f49ddbd503ae
Source dataset
uspto-grants-2009_04
Patent number
US07521461B2

Reaction notes

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