Triethylamine → HCID 18348591, compound

HRID 2268469Notes

Reaction equation

HRID 2268469 reaction equation
[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[C:10]([O:14][CH3:15])[C:9]([O:16][CH3:17])=[C:8]2[C:4]=1[CH2:5][CH2:6][CH:7]2[CH2:18][CH2:19][CH2:20][CH2:21][O:22][C:23]1[CH:31]=[CH:30]C(C(O)=O)=[CH:25][CH:24]=1.[Cl-].C[NH2+]C.Cl.C(N=C=NCCCN(C)C)C.O.[OH:49]N1C2C=CC=CC=2N=N1.[CH2:59]([N:61]([CH2:64]C)[CH2:62][CH3:63])C>O.C1COCC1>[CH3:64][N:61]([CH3:59])[C:62](=[O:49])[C:63]1[CH:30]=[CH:31][C:23]([O:22][CH2:21][CH2:20][CH2:19][CH2:18][CH:7]2[CH2:8][C:4]3[C:5](=[C:9]([O:16][CH3:17])[C:10]([O:14][CH3:15])=[C:11]([O:12][CH3:13])[C:3]=3[O:2][CH3:1])[CH2:6]2)=[CH:24][CH:25]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 12954980Dimethylazanium;chlorideHCID 18348660HCID 18348660, compound

Product 1

HCID 18348591HCID 18348591, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A THF (16 ml) suspension of 4-[4-(4,5,6,7-tetramethoxyindan-1-yl)butoxy]benzoic acid (400 mg, 0.929 mmols), dimethylammonium chloride (150 mg, 1.86 mmols), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (357 mg, 1.86 mmols), 1-hydroxybenzotriazole monohydrate (285 mg, 1.86 mmols) and triethylamine (0.777 ml, 5.57 mmols) was stirred at room temperature for 12 hours. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, and then dried. The solvent was evaporated out in vacuo, and the resulting crude product was purified by alumina column chromatography (ethyl acetate) followed by recrystallization (from hexane-ethyl acetate) to obtain the entitled compound (408 mg) as crystals.

Workup

  1. extractionwas then extracted with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  3. customdried
  4. customThe solvent was evaporated out in vacuo
  5. customthe resulting crude product was purified by alumina column chromatography (ethyl acetate)
  6. customfollowed by recrystallization (from hexane-ethyl acetate)

Sources & evidence

ORD record
ord-795d4e0fc2d64b37834a39405f07844b
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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