1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 68288400, compound

HRID 541330Notes

Reaction equation

HRID 541330 reaction equation
[CH2:1]([C:3]1[CH:11]=[C:10]([CH2:12][CH3:13])[C:9]([C:14]([O:16][CH3:17])=[O:15])=[CH:8][C:4]=1[C:5]([OH:7])=O)[CH3:2].Cl.[NH:19]1[CH2:24][CH2:23][CH:22]([C:25]2[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[CH:27][CH:26]=2)[CH2:21][CH2:20]1.CCN=C=NCCCN(C)C.Cl>CN(C)C1C=CN=CC=1.CN(C)C=O.C(OCC)(=O)C>[C:29]([C:28]1[CH:27]=[CH:26][C:25]([CH:22]2[CH2:23][CH2:24][N:19]([C:5]([C:4]3[C:3]([CH2:1][CH3:2])=[CH:11][C:10]([CH2:12][CH3:13])=[C:9]([CH:8]=3)[C:14]([O:16][CH3:17])=[O:15])=[O:7])[CH2:20][CH2:21]2)=[CH:32][CH:31]=1)#[N:30]

Participants

7

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 193916184-(Piperidin-4-yl)benzonitrile--hydrogen chloride (1/1)2×HCID 68288341HCID 68288341, compound2×

Product 1

HCID 68288400HCID 68288400, compoundYield 60%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

To a round-bottom flask, were added a solution of 2,4-diethyl-5-(methoxycarbonyl)benzoic acid (compound 204.5, 500 mg, 2.12 mmol, 1.00 equiv), 4-(piperidin-4-yl)benzonitrile hydrochloride (compound 1.5, 470 mg, 2.12 mmol, 1 equiv), EDC.HCl (810 mg, 4.24 mmol, 2.00 equiv), and 4-dimethylaminopyridine (520 mg, 4.24 mmol, 2 equiv) in N,N-dimethylformamide (15 mL). The reaction was stirred overnight at 25° C. Upon reaction completion, the reaction mixture was diluted with 30 mL of ethyl acetate, then washed with 1×20 mL of NH4Cl (aq.) and 1×20 mL of brine. The organic phase was dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography with a solvent mixture of ethyl acetate and petroleum ether (1:1) to yield 500 mg (60%) of the title compound as a pale yellow solid.

Workup

  1. customUpon reaction completion
  2. washwashed with 1×20 mL of NH4Cl (aq.) and 1×20 mL of brine
  3. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel chromatography with a solvent mixture of ethyl acetate and petroleum ether (1:1)

Sources & evidence

ORD record
ord-10461bb6bebf4d569f6e1a56766779a9
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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