Diethylamine → HCID 19608225, compound

HRID 745062Notes

Reaction equation

HRID 745062 reaction equation
[C:1]([CH2:4][CH2:5][C:6]([NH:8][C:9]1[CH:27]=[CH:26][C:12]([C:13]([N:15]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[CH2:19][CH2:18][CH2:17][CH2:16]2)=[O:14])=[CH:11][CH:10]=1)=[O:7])(O)=[O:2].P(C#N)(OCC)(OCC)=O.[CH2:38]([NH:40][CH2:41][CH3:42])[CH3:39]>CN(C)C=O.C(N(CC)CC)C>[CH2:38]([N:40]([CH2:41][CH3:42])[C:1]([CH2:4][CH2:5][C:6]([NH:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]([N:15]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[CH2:19][CH2:18][CH2:17][CH2:16]2)=[O:14])=[CH:26][CH:27]=1)=[O:7])=[O:2])[CH3:39]

Participants

6

Reactant 3

HCID 8021DiethylamineHCID 76257Diethyl cyanophosphonateHCID 19607810HCID 19607810, compound

Product 1

HCID 19608225HCID 19608225, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8471TriethylamineSolvent

Procedure

1-[4-(3-Carboxypropionylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.5 g) is dissolved in dimethylformamide (1 ml) and thereto is added dropwise diethyl cyanophosphate (0.25 g) under ice-cooling. The mixture is stirred at room temperature for 30 minutes and then cooled again with ice. Thereto are added dropwise a solution of diethylamine (0.11 g) in dimethylformamide (1 ml) and triethylamine (0.34 g). The mixture is stirred at room temperature for 16 hours. The solvent is distilled off under reduced pressure and water is added to the resulting residue. The mixture is extracted with dichloromethane. The organic layer is washed successively with diluted hydrochloric acid, water, saturated sodium hydrogen carbonate solution, water and saturated saline solution, and dried over magnesium sulfate. The solvent is distilled off under reduced pressure and the resulting residue is purified by silica gel column chromatography (eluent; ethyl acetate), and recrystallized from n-hexane/ethyl acetate to give 1-[4-(3-diethylaminocarbonylpropionylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.42 g) as colorless scales, m.p. 165°-167° C.

Workup

  1. temperaturecooling
  2. temperaturecooled again with ice
  3. stirringThe mixture is stirred at room temperature for 16 hours
  4. distillationThe solvent is distilled off under reduced pressure and water
  5. additionis added to the resulting residue
  6. extractionThe mixture is extracted with dichloromethane
  7. washThe organic layer is washed successively with diluted hydrochloric acid, water, saturated sodium hydrogen carbonate solution, water and saturated saline solution
  8. dry with materialdried over magnesium sulfate
  9. distillationThe solvent is distilled off under reduced pressure
  10. customthe resulting residue is purified by silica gel column chromatography (eluent; ethyl acetate)
  11. customrecrystallized from n-hexane/ethyl acetate

Sources & evidence

ORD record
ord-afa6bdbc2b14465d8e23dd0d750ea1ed
Source dataset
uspto-grants-1996_09
Patent number
US05559230

Reaction notes

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