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Urea → N-[2-(4-Carbomethoxyphenyl)-1-methylethyl]-2-hydroxy-2-(4-methyl-oxazol-5-yl)ethanamine dihydrochloride

HRID 1451413
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1451413
[CH3:1][C:2]1[N:3]=[CH:4][O:5][C:6]=1[C:7](=[O:10])[CH2:8]Br.C(N(CC)C(C)C)(C)C.[C:20]([C:24]1[CH:29]=[CH:28][C:27]([CH2:30][CH:31]([NH2:33])[CH3:32])=[CH:26][CH:25]=1)([O:22][CH3:23])=[O:21].NC(N)=O.[BH4-].[Na+].C(Cl)[Cl:41]>CO>[ClH:41].[ClH:41].[C:20]([C:24]1[CH:29]=[CH:28][C:27]([CH2:30][CH:31]([NH:33][CH2:8][CH:7]([OH:10])[C:6]2[O:5][CH:4]=[N:3][C:2]=2[CH3:1])[CH3:32])=[CH:26][CH:25]=1)([O:22][CH3:23])=[O:21]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 6

HCID 1176UreaHCID 6344Dichloromethane2×HCID 81531DiisopropylethylamineHCID 4311764Sodium borohydrideHCID 15034329Methyl 4-(2-aminopropyl)benzoateHCID 199743052-Bromo-1-(4-methyloxazol-5-yl)ethanone

Produkt 1

HCID 14076231
N-[2-(4-Carbomethoxyphenyl)-1-methylethyl]-2-hydroxy-2-(4-methyl-oxazol-5-yl)ethanamine dihydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
35 °C

Versuchsvorschrift

2.6 g (0.009 mol) of 4-Methyl-5-bromoacetyl-oxazole and 1.16 g (0.009 mol) of N,N-diisopropyl-ethylamine are dissolved in 50 ml of methylene chloride. This solution is added dropwise, within 20 minutes to 3.47 g (0.018 mol) of 2-(4-carbomethoxyphenyl)-1-methylethylamine in 100 ml of methylene chloride, and the mixture is stirred at room temperature for 2 hours and at 35° C. for 1 hour. The reaction solution is cooled in an ice bath, and 150 ml of methanol are added. Then, for the reduction of the resulting amino-ketone, 1 g of sodium borohydride is added in portions over 30 minutes, and the mixture is stirred at room temperature for 20 hours and then evaporated. Ice-water is then added to the residue, and the mixture is acidified with hydrochloric acid, made alkaline with concentrated aqueous ammonia and extracted with chloroform. The extract is dried over sodium sulphate, concentrated and purified on a silica gel column using ethyl acetate/methanol=9:1 as eluant. The hydrochloride is then precipitated with ethereal hydrochloric acid.

Aufarbeitung

  1. temperatureThe reaction solution is cooled in an ice bath
  2. stirringthe mixture is stirred at room temperature for 20 hours
  3. customevaporated
  4. additionIce-water is then added to the residue
  5. extractionextracted with chloroform
  6. dry with materialThe extract is dried over sodium sulphate
  7. concentrationconcentrated
  8. custompurified on a silica gel column
  9. customThe hydrochloride is then precipitated with ethereal hydrochloric acid

Quellen und Nachweise

ORD-Eintrag
ord-a4424c628b90477b9dd25b5dedc648d7
Quelldatensatz
uspto-grants-1997_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05604225

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