Triethylamine → 2-Bromo-N-(2,4-difluorobenzyl)-N-heptylacetamide

HRID 898894Notes

Reaction equation

HRID 898894 reaction equation
[F:1][C:2]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:3]=1[CH2:4][NH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C(N(CC)CC)C.[Br:25][CH2:26][C:27](Cl)=[O:28]>C(Cl)Cl>[Br:25][CH2:26][C:27]([N:5]([CH2:4][C:3]1[CH:13]=[CH:14][C:15]([F:17])=[CH:16][C:2]=1[F:1])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[O:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 89602Bromoacetyl chlorideHCID 60663854N-(2,4-difluorobenzyl)-N-heptylamine

Product 1

HCID 692602152-Bromo-N-(2,4-difluorobenzyl)-N-heptylacetamideYield 80.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(2,4-difluorobenzyl)-N-heptylamine (2.004 g, 8.304 mmol) was dissolved in DCM (30 ml). It was then cooled in an ice-bath. Triethylamine (1.092 g, 10.796 mmol) was added and then bromacetyl chloride (1.438 g, 9.135 mmol) was dropped in. The mixture was stirred for 2 hours (ice-bath). It was then washed with water (with additional of 1% hydrochloric acid, pH-3), water and brine, and dried (magnesium sulphate) and evaporated. The crude oil product was dissolved in DCM, then loaded onto a column (ISOLUTE®SI 5 g/25 ml) and eluted with more DCM. Oil product 2.412 g was obtained, yield 80%

Workup

  1. temperatureIt was then cooled in an ice-bath
  2. washIt was then washed with water (with additional of 1% hydrochloric acid, pH-3), water and brine
  3. dry with materialdried (magnesium sulphate)
  4. customevaporated
  5. dissolutionThe crude oil product was dissolved in DCM
  6. washeluted with more DCM

Sources & evidence

ORD record
ord-23ad5e5761c045d79bb0dba95df55315
Source dataset
uspto-grants-2008_04
Patent number
US07351858B2

Reaction notes

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