Cuminaldehyde → N-(3-ethoxypropyl)-N-(4-isopropylbenzyl)amine

HRID 899888

Reaktionsgleichung

Reaktionsgleichung von HRID 899888
[CH:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].C(OC)(OC)OC.[CH2:19]([O:21][CH2:22][CH2:23][CH2:24][NH2:25])[CH3:20].[BH4-]>CO.C(Cl)Cl.C(O)(=O)C>[CH2:19]([O:21][CH2:22][CH2:23][CH2:24][NH:25][CH2:8][C:7]1[CH:10]=[CH:11][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:5][CH:6]=1)[CH3:20]

Komponenten

8

Edukt 4

HCID 326CuminaldehydeHCID 9005Trimethyl orthoformateHCID 22720Propanolamine ethyl etherHCID 28123Borohydride

Produkt 1

HCID 4723366N-(3-ethoxypropyl)-N-(4-isopropylbenzyl)amineAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

p-iso-Propylbenzaldehyde (1.007 g, 6.798 mmol) was dissolved in methanol (5 ml). Trimethyl orthoformate (5 ml) was added. 3-Ethoxypropylamine (681 mg, 6.6 mmol) was then added and followed by acetic acid (0.2 ml). After standing at room temperature overnight, DCM (5 ml) was added and followed by borohydride on polymer support (5.28 g, 13.2 mmol). The mixture was shaken at room temperature for 4 days and then filtered. The filtrate was evaporated. The residue was dissolved in acetonitrile, then divided into two portions and loaded on 2 columns (ISOLUTE® PRS, 10 g/70 ml, wetted with acetonitrile). It was eluted with acetonitrile, then methanol and then methanol (NH3 sat.). The product fractions were combined and evaporated. Oil product 1.283 g was obtained, yield 83%.

Aufarbeitung

  1. filtrationfiltered
  2. customThe filtrate was evaporated
  3. dissolutionThe residue was dissolved in acetonitrile
  4. washIt was eluted with acetonitrile
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-9a66f51ee2ca4707be01d5c6e0b6db42
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07355069B2

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