Cycloheptylamine → HCID 13145543, compound

HRID 1588249Notes

Reaction equation

HRID 1588249 reaction equation
[CH:1]1([NH2:8])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.Br[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19].C(Cl)[Cl:24]>>[ClH:24].[CH2:21]([O:20][C:18](=[O:19])[CH2:17][NH:8][CH:1]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[CH3:22]

Participants

5

Reactant 4

HCID 2899CycloheptylamineHCID 6344DichloromethaneHCID 7748Ethyl bromoacetateHCID 8471Triethylamine

Product 1

HCID 13145543HCID 13145543, compoundYield 47%

Procedure

In a 2 liter erlenmeyer flask was placed 49.8 g (0.44 mole) of cycloheptylamine, 66.6 g (0.66 mole) of triethylamine and 1 liter of methylene chloride. The resulting solution was stirred, while 73.4 g (0.44 mole) of ethyl bromoacetate was added dropwise. The mixture was stirred for 16 hours at room temperature and then filtered. The filtrate was washed with water (3×200 mL), dried over magnesium sulfate, filtered and solvent was removed by rotary evaporation. The resulting oil was run through a short column with the eluent being first methylene chloride and then methylene chloride containing 0.25% ammonium hydroxide and 2.5% methanol. A small amount of a fast moving impurity was separated from the bulk of the product. Solvent was again removed from the product by rotary evaporation and the resulting oil was dissolved in ether, dried over magnesium sulfate and filtered. Hydrogen chloride saturated ether was then added to the filtrate and the resulting precipitate was filtered off and dried in vacuum to give 47.8 g (47%) of N-cycloheptylglycine ethyl ester hydrochloride.

Workup

  1. customIn a 2 liter erlenmeyer flask was placed
  2. additionwas added dropwise
  3. filtrationfiltered
  4. washThe filtrate was washed with water (3×200 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customsolvent was removed by rotary evaporation
  8. customwas separated from the bulk of the product
  9. customSolvent was again removed from the product by rotary evaporation
  10. dissolutionthe resulting oil was dissolved in ether
  11. dry with materialdried over magnesium sulfate
  12. filtrationfiltered
  13. additionHydrogen chloride saturated ether was then added to the filtrate
  14. filtrationthe resulting precipitate was filtered off
  15. customdried in vacuum

Sources & evidence

ORD record
ord-b1be5d3df0304e57a33ff77e8b4fdeb0
Source dataset
uspto-grants-1993_06
Patent number
US05221665

Reaction notes

Loading…