N,N'-Bis(1-methylethyl)urea → 1-(N-methyl,N-isopropylamino)-3,5-dimethyl-adamantane hydrochloride

HRID 1112399

Reaktionsgleichung

Reaktionsgleichung von HRID 1112399
[ClH:1].Br[C:3]12[CH2:12][C:7]3([CH3:13])[CH2:8][CH:9]([CH2:11][C:5]([CH3:14])([CH2:6]3)[CH2:4]1)[CH2:10]2.[CH:15]([NH:18][C:19](NC(C)C)=O)([CH3:17])[CH3:16]>O>[ClH:1].[CH3:19][N:18]([C:3]12[CH2:12][C:7]3([CH3:13])[CH2:8][CH:9]([CH2:11][C:5]([CH3:14])([CH2:6]3)[CH2:4]1)[CH2:10]2)[CH:15]([CH3:17])[CH3:16]

Komponenten

4

Edukt 2

HCID 20084N,N'-Bis(1-methylethyl)ureaHCID 227639521-Bromo-3,5-dimethyl-adamantane hydrochloride

Produkt 1

HCID 227639501-(N-methyl,N-isopropylamino)-3,5-dimethyl-adamantane hydrochlorideAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

2.43 grams of 1-bromo-3,5-dimethyl-adamantane hydrochloride were heated in a closed vessel for 40 minutes at 180° C., with 2.8 grams of N,N'-di-isopropylurea. After cooling, the reaction product was suspended in 50 ml. of water, acidified, and extracted with two 10-ml. portions of ether. Next, the water phase was brought to a pH of between 12 and 13 with sodium hydroxide, stirred for 10 minutes, and extracted with four 10-ml. portions of benzene. The benzene extracts were combined, the benzene stripped off, and the residue refluxed for 10 hours with 4 ml. of a 32% formaldehyde solution and 4 ml. of concentrated formic acid. After cooling, the solution was worked up as in Example 6. It yielded 1.04 grams of 1-(N-methyl,N-isopropylamino)-3,5-dimethyl-adamantane hydrochloride. Yield: 38% of theoretical yield.

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionextracted with two 10-ml
  3. extractionextracted with four 10-ml
  4. temperaturethe residue refluxed for 10 hours with 4 ml
  5. temperatureAfter cooling

Quellen und Nachweise

ORD-Eintrag
ord-26cf6679e4704e929b7a692564565253
Quelldatensatz
uspto-grants-1978_10
Patentnummer
US04122193

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