Triethylamine → HCID 68489904, compound

HRID 1039193Notes

Reaction equation

HRID 1039193 reaction equation
Cl.CN(C)CCCN=C=NCC.[CH3:13][O:14][C:15](=[O:23])[CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=O.Cl.[NH2:25][CH2:26][C:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[O:35][CH3:36])=[O:28].C(N(CC)CC)C>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:13][O:14][C:15](=[O:23])[CH2:16][CH2:17][CH2:18][CH2:19][C:20](=[O:22])[NH:25][CH2:26][C:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[O:35][CH3:36])=[O:28]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 12328monoMethyl adipateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 222815712-Amino-1-(2-methoxyphenyl)ethan-1-one hydrochloride

Product 1

HCID 68489904HCID 68489904, compoundYield 80.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Dissolve 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (3.57 g, 18.62 mmol), 4-(dimethylamino)pryidine (463.8 mg, 3.79 mmol) and adipic acid monomethyl ester (2.97 g, 18.55 mmol) in 100 mL of CH2Cl2 and allow it to stir at room temperature for 45 minutes. Add crude 2-amino-1-(2-methoxy-phenyl)-ethanone hydrochloride (3.74 g, 18.55 mmol) and triethylamine (3.75 g, 37.1 mmol) to the reaction mixture and allow it to stir at ambient temperature for 22 hours. Dilute the reaction with 200 mL of CH2Cl2 and wash it with 1 N HCl (2×), saturated aqueous NaHCO3 (2×) and brine (1×). Dry the organic layer with MgSO4. Filter the drying agent and concentrate in vacuo to afford 4.57 g of the titled product (80%): mass spectrum: m/z=308.1 (M+H).

Workup

  1. stirringto stir at ambient temperature for 22 hours
  2. additionDilute
  3. washwash it with 1 N HCl (2×), saturated aqueous NaHCO3 (2×) and brine (1×)
  4. dry with materialDry the organic layer with MgSO4
  5. filtrationFilter the drying agent
  6. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-5da518efbce8425db72fa73fa8837ede
Source dataset
uspto-grants-2013_10
Patent number
US08552039B2

Reaction notes

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