2,4-Dimethoxybenzoic acid → 2,4-Dimethoxy-N-[4-[2-(1-pyrrolidinyl)ethoxy]benzyl]benzamide

HRID 703530Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 703530
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=O.ClC(OCC)=O.C(N(CC)CC)C.[N:27]1([CH2:32][CH2:33][O:34][C:35]2[CH:42]=[CH:41][C:38]([CH2:39][NH2:40])=[CH:37][CH:36]=2)[CH2:31][CH2:30][CH2:29][CH2:28]1>O1CCCC1>[CH3:1][O:2][C:3]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:4]=1[C:5]([NH:40][CH2:39][C:38]1[CH:37]=[CH:36][C:35]([O:34][CH2:33][CH2:32][N:27]2[CH2:31][CH2:30][CH2:29][CH2:28]2)=[CH:42][CH:41]=1)=[O:7]

Komponenten

6

Edukt 4

HCID 70522,4-Dimethoxybenzoic acidHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 14425929(4-(2-(Pyrrolidin-1-yl)ethoxy)phenyl)methanamine

Produkt 1

HCID 151369702,4-Dimethoxy-N-[4-[2-(1-pyrrolidinyl)ethoxy]benzyl]benzamideAusbeute 94,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a cooled suspension of 1.82 g of 2,4-dimethoxybenzoic acid in 10 ml of tetrahydrofuran was added 1.09 g of ethyl chloroformate and 1.01 g of triethylamine. After stirring for 15 minutes, to the mixture was added a solution of 2.00 g of 4-[2-(1-pyrrolidinyl)ethoxy]benzylamine in 5 ml of tetrahydrofuran. The mixture was stirred for 15 minutes and the solvent was evaporated. To the residue was added 10% hydrochloric acid, and the solution was washed with ethyl acetate. The aqueous layer was made alkaline with potassium carbonate and was extracted with ethyl acetate. The extract was washed with water, dried, and evaporated to give 3.31 g of the title compound as a colorless oil.

Aufarbeitung

  1. stirringThe mixture was stirred for 15 minutes
  2. customthe solvent was evaporated
  3. additionTo the residue was added 10% hydrochloric acid
  4. washthe solution was washed with ethyl acetate
  5. extractionwas extracted with ethyl acetate
  6. washThe extract was washed with water
  7. customdried
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-54efb37a0da744b6a2b62880d8ae6258
Quelldatensatz
uspto-grants-1991_01
Patentnummer
US04983633

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