Acetic Acid → 7-chloro-N-cyclopropyl-2,3-dihydro-1H-inden-1-amine

HRID 2194985Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2194985
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.C(O)(=O)C.[Cl:9][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:18]=1[C:17](=O)[CH2:16][CH2:15]2.C([BH3-])#N.[Na+]>CO>[Cl:9][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:18]=1[CH:17]([NH:4][CH:1]1[CH2:3][CH2:2]1)[CH2:16][CH2:15]2

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 69828CyclopropylamineHCID 5003444Sodium cyanoborohydrideHCID 112174497-CHLORO-1-INDANONE

Produkt 1

HCID 684283077-chloro-N-cyclopropyl-2,3-dihydro-1H-inden-1-amineAusbeute 89,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a cooled solution of 4.16 ml (60 mmol) of cyclopropylamine and 4.3 ml (75 mmol) of acetic acid, together with 5 g of 3 Å molecular sieves, in 80 ml of methanol, are added 5 g (30 mmol) of 7-chloro-2,3-dihydro-1H-inden-1-one. The reaction mixture is stirred for 4 hrs at reflux. The reaction mixture is then cooled to ambient temperature and 2.83 g (45 mmol) of sodium cyanoborohydride are slowly added. The reaction mixture is further stirred for 2 hrs at reflux. The solvent is removed under vacuum and 100 ml of water are then added to the residue and the pH is adjusted to 10 with sodium hydroxyde. The watery layer is extracted three times with dichloromethane (3×50 ml); the combined organic layers are dried over magnesium sulphate and concentrated in vacuum to yield 5.6 g (80% yield) of 7-chloro-N-cyclopropyl-2,3-dihydro-1H-inden-1-amine as an brown oil (M+1=208).

Aufarbeitung

  1. temperatureat reflux
  2. stirringThe reaction mixture is further stirred for 2 hrs
  3. temperatureat reflux
  4. customThe solvent is removed under vacuum and 100 ml of water
  5. additionare then added to the residue
  6. extractionThe watery layer is extracted three times with dichloromethane (3×50 ml)
  7. dry with materialthe combined organic layers are dried over magnesium sulphate
  8. concentrationconcentrated in vacuum

Quellen und Nachweise

ORD-Eintrag
ord-9758f4da96df4d5ca1e3b8b40fb6a742
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08334390B2

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