Water → HCID 178512092, compound

HRID 714408Notes

Reaction equation

HRID 714408 reaction equation
Cl.C(O[C:5](=[NH:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)C.C(N(CC)CC)C.[CH2:20]([NH2:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>CN(C)C=O.C(OCC)(=O)C>[C:21]1([CH2:20][NH:27][C:5]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)=[NH:12])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7504BenzylamineHCID 8471TriethylamineHCID 79249Benzenecarboximidic acid, ethyl ester, hydrochloride (1:1)

Product 1

HCID 178512092HCID 178512092, compoundYield 115.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of ethylbenzimidate hydrochloride (3.0 g, 16.2 mmol) in N,N-dimethylformamide (10 mL) was added triethylamine (1.60 g, 16.2 mmol). The reaction mixture was allowed to stir at room temperature for 1 h and then filtered to remove triethylamine salts, which were rinsed with N,N-dimethylformamide (5 mL). Benzylamine (1.23 g, 11.5 mmol) was added to the filtrate, and the mixture was heated to 65° C. for 24 h. To the cooled mixture was added water (80 mL) and ethyl acetate. The organic layer was washed with water and brine, then dried (MgSO4) and concentrated under reduced pressure to afford the title product as a clear oil (2.80 g).

Workup

  1. filtrationfiltered
  2. customto remove triethylamine salts, which
  3. washwere rinsed with N,N-dimethylformamide (5 mL)
  4. temperaturethe mixture was heated to 65° C. for 24 h
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-98fbf23045a945198e26e1330d1c266a
Source dataset
uspto-grants-2015_11
Patent number
US09187432B2

Reaction notes

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