1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 69736810, compound

HRID 897213Notes

Reaction equation

HRID 897213 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][C:10]([F:13])([F:12])[F:11])=[CH:4][CH:3]=1.[C:14]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])(=[O:19])[CH2:15][C:16]([O-])=[O:17].Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.C(OCC)(=O)C>[C:21]([O:20][C:14](=[O:19])[CH2:15][C:16]([N:8]([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)[CH2:9][C:10]([F:11])([F:12])[F:13])=[O:17])([CH3:24])([CH3:23])[CH3:22]

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10420625(4-Chlorophenyl) (2,2,2-trifluoroethyl)amineHCID 21883978Tert-butyl malonate

Product 1

HCID 69736810HCID 69736810, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

(4-Chlorophenyl) (2,2,2-trifluoroethyl)amine (1.84 g, 8.8 mmol) and mono-t-butyl malonate (1.37 mL, 8.9 mmol) were dissolved in DCM (50 mL) and the solution cooled in an ice bath prior to portion wise addition of 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (1.71 g, 8.9 mmol). After one hour the reaction was complete by TLC and was diluted with ethyl acetate and sequentially washed with 1 N NaOH, 1N HCl, and brine. The organic layer was dried with MgSO4 and concentrated under reduced pressure to give a white solid which was used without further purification. 1H NMR (300 MHz, CDCl3) δ ppm 1.40 (9H, s), 3.13 (2H, s), 4.34 (2H, q, J=8.7 Hz), 7.22 (2H, m), 7.41 (2H, m).

Workup

  1. temperaturethe solution cooled in an ice bath
  2. washsequentially washed with 1 N NaOH, 1N HCl, and brine
  3. dry with materialThe organic layer was dried with MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customto give a white solid which
  6. customwas used without further purification

Sources & evidence

ORD record
ord-1d2b756f07374dac88d23db7cfe0145c
Source dataset
uspto-grants-2005_07
Patent number
US06921821B2

Reaction notes

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