N,N-Diethylethylenediamine → HCID 88138733, compound

HRID 1614630Notes

Reaction equation

HRID 1614630 reaction equation
[CH2:1]([N:3]([CH2:7][CH3:8])[CH2:4][CH2:5][NH2:6])[CH3:2].[C:9]([N:16]1[CH:20]=[CH:19]N=[CH:17]1)(N1C=CN=C1)=[O:10].[F:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][CH:29]([C:36]2[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=2)[CH:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)=[CH:24][CH:23]=1>O1CCCC1.C(Cl)Cl>[OH2:10].[CH2:1]([N:3]([CH2:7][CH3:8])[CH2:4][CH2:5][NH:6][C:9]([N:16]1[CH2:17][CH2:31][CH:30]([CH:29]([C:36]2[CH:37]=[CH:38][C:39]([F:42])=[CH:40][CH:41]=2)[NH:28][C:25]2[CH:24]=[CH:23][C:22]([F:21])=[CH:27][CH:26]=2)[CH2:19][CH2:20]1)=[O:10])[CH3:2].[CH2:1]([N:3]([CH2:4][CH2:5][NH:6][C:9]([N:33]1[CH2:34][CH2:35][CH:30]([CH:29]([NH:28][C:25]2[CH:24]=[CH:23][C:22]([F:21])=[CH:27][CH:26]=2)[C:36]2[CH:37]=[CH:38][C:39]([F:42])=[CH:40][CH:41]=2)[CH2:31][CH2:32]1)=[O:10])[CH2:7][CH3:8])[CH3:2]

Participants

6

Reactant 3

HCID 60993N,N-DiethylethylenediamineHCID 682631,1'-CarbonyldiimidazoleHCID 19771957N,alpha-bis(4-fluorophenyl)-4-piperidinemethanamine

Product 1

HCID 88138733HCID 88138733, compoundYield 124.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of N,N-diethylethylenediamine (1.63 g, 0.014 mol) and 1,1'-carbonyldiimidazole (2.43 g, 0.015 mol) in 100 mL of tetrahydrofuran was stirred at room temperature under nitrogen for 2 h. A solution of N,α-bis(4-fluorophenyl)-4-piperidinemethanamine (3.76 g, 0.01245 mol) was added. The resulting solution was heated at reflux 16 h under nitrogen. The solution was cooled to room temperature and concentrated to dryness. The brown residue obtained was dissolved in methylene chloride. The methylene chloride layer was extracted with water, dried (Na2SO4), and filtered. The methylene chloride was removed with a rotary evaporator to give a dark brown oil (5.63 g). This material was dissolved in methylene chloride and placed on a silica gel column for flash chromatography. The column was eluted with 20% methanol-ethyl acetate, 50% methanol-ethyl acetate, and methanol. Fractions of similar purity were combined and solvents removed to give a dark brown oil. This material was dried for 16 h at 100° C. in the presence of phosphorus pentoxide. The procedure provided 4.21 g (74.2%) of a dark brown glass.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux 16 h under nitrogen
  3. concentrationconcentrated to dryness
  4. customThe brown residue obtained
  5. extractionThe methylene chloride layer was extracted with water
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customThe methylene chloride was removed with a rotary evaporator

Sources & evidence

ORD record
ord-1cc6cbe88fa946c588a34c5c03561995
Source dataset
uspto-grants-1993_03
Patent number
US05198449

Reaction notes

Loading…