Triethylamine → HCID 69851475, compound

HRID 2307449Notes

Reaction equation

HRID 2307449 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][CH:13]=1)[CH:6]=[CH:7][C:8]([OH:10])=O.[O:14]1[C:18]2[CH:19]=[CH:20][C:21]([CH:23]([NH2:25])[CH3:24])=[CH:22][C:17]=2[O:16][CH2:15]1.CCN=C=NCCCN(C)C.Cl.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.C(Cl)Cl.O>[O:14]1[C:18]2[CH:19]=[CH:20][C:21]([CH:23]([NH:25][C:8](=[O:10])[CH:7]=[CH:6][C:5]3[CH:11]=[CH:12][CH:13]=[C:3]([O:2][CH3:1])[CH:4]=3)[CH3:24])=[CH:22][C:17]=2[O:16][CH2:15]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 871552-Propenoic acid, 3-(3-methoxyphenyl)-HCID 1294981-(2H-1,3-Benzodioxol-5-yl)ethan-1-amineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 69851475HCID 69851475, compoundYield 78%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-methoxycinnamic acid (2 mmole), (±)-1-benzo[1,3]dioxol-5-yl-ethylamine, Preparation 2 (396 mg, 2.4 mmole), EDC hydrochloride (768 mg, 4 mmole), DMAP (244 mg, 2 mmole), and triethylamine (404 mg, 4 mmole) in CH2Cl2 (5 mL) was stirred at room temperature for 16 hours. Water was added, and the mixture was extracted with CH2Cl2 (three times). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated in vacuo. The crude product was subjected to purification by flash column chromatography on silica gel eluted with EtOAc/hexane (2:1) to provide the racemic titled compound (510 mg, 78%).

Workup

  1. extractionthe mixture was extracted with CH2Cl2 (three times)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe crude product was subjected to purification by flash column chromatography on silica gel
  7. washeluted with EtOAc/hexane (2:1)

Sources & evidence

ORD record
ord-d83eb8cbcfe44f33a0d262db2f423be5
Source dataset
uspto-grants-2004_12
Patent number
US06831080B2

Reaction notes

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