N,N-Dimethyl-1,3-propanediamine → HCID 22799977, Verbindung

HRID 1438734Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1438734
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[O:6][C@H:7]([C:16]([OH:18])=O)[O:8][C@H:9]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:4]=2[CH:3]=1.N[C@H](C(Cl)=O)CCSCC.[CH3:31][N:32]([CH2:34][CH2:35][CH2:36][NH2:37])[CH3:33]>CN(C=O)C.C(Cl)Cl>[ClH:1].[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[O:6][C@H:7]([C:16]([NH:37][CH2:36][CH2:35][CH2:34][N:32]([CH3:33])[CH3:31])=[O:18])[O:8][C@H:9]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:4]=2[CH:3]=1

Komponenten

6

Edukt 3

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 12812406HCID 12812406, VerbindungHCID 54437745HCID 54437745, Verbindung

Produkt 1

HCID 22799977HCID 22799977, VerbindungAusbeute 162,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

cis-6-Chloro-4-phenyl-1,3-benzodioxan-2-carboxylic acid (2.91 g., 10 mmoles), ethionyl chloride (10 ml) and dry DMF (4 drops) were refluxed in 100 ml of dry CH2Cl2 for 2 hrs. Removal of solvent and excess reagent under reduced pressure afforded the crude acid chloride which was then redissolved in CH2Cl2 (50 ml) and treated with dimethylaminopropyl amine (1.53 g., 15 mmloes). The reaction was somewhat exothermic and the stirred mixture was maintained at 20° for 35 mins., and then at reflux for 45 mins. After solvent removal, the residue was partitioned between 5% Na2CO3 solution and CH2Cl2 (2 portions). The organics were then washed with brine, dried (MgSO4) and treated with HClg. Solvent removal and crystallization of the residue from isopropyl alcohol gave the product as a white solid (3.34 g., 81.3%). Recrystallization from abs EtOH:Et2O afforded pure material (mp 213° -216° d).

Aufarbeitung

  1. customRemoval of solvent and excess reagent under reduced pressure
  2. customafforded the crude acid chloride which
  3. temperaturethe stirred mixture was maintained at 20° for 35 mins
  4. temperature, and then at reflux for 45 mins
  5. customAfter solvent removal
  6. customthe residue was partitioned between 5% Na2CO3 solution and CH2Cl2 (2 portions)
  7. washThe organics were then washed with brine
  8. dry with materialdried (MgSO4)
  9. additiontreated with HClg
  10. customSolvent removal and crystallization of the residue from isopropyl alcohol

Quellen und Nachweise

ORD-Eintrag
ord-7aa178f89e9346578f95ee4968824474
Quelldatensatz
uspto-grants-1977_11
Patentnummer
US04056540

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