Butylamine → (E)-N-(6,6-Dimethyl-2-hepten-4-ynyl)-N-ethyl-3-(3-(3-thienyl)benzyloxy]benzylamine hydrochloride

HRID 487789

Reaktionsgleichung

Reaktionsgleichung von HRID 487789
[Cl:1]/[CH:2]=[CH:3]/[CH2:4][N:5]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]3[CH:27]=[CH:26][S:25][CH:24]=3)[CH:18]=2)[CH:10]=1)[CH2:6][CH3:7].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N)CCC.[C:52]([C:56]#[CH:57])([CH3:55])([CH3:54])[CH3:53]>[Cu]I.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O1CCCC1>[ClH:1].[CH3:53][C:52]([CH3:55])([CH3:54])[C:56]#[C:57]/[CH:2]=[CH:3]/[CH2:4][N:5]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]3[CH:27]=[CH:26][S:25][CH:24]=3)[CH:18]=2)[CH:10]=1)[CH2:6][CH3:7]

Komponenten

8

Edukt 4

HCID 8007ButylamineHCID 11776TriphenylphosphineHCID 135123,3-Dimethyl-1-butyneHCID 19917481(E)-N-(3-chloro-2-propenyl)-N-ethyl-3-[3-(3-thienyl)benzyloxy]benzylamine

Produkt 1

HCID 19917490(E)-N-(6,6-Dimethyl-2-hepten-4-ynyl)-N-ethyl-3-(3-(3-thienyl)benzyloxy]benzylamine hydrochlorideAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 167845palladium(II) acetateKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To 2.7 ml of tetrahydrofuran were added 360 mg (0.90 mmol) of (E)-N-(3-chloro-2-propenyl)-N-ethyl-3-[3-(3-thienyl)benzyloxy]benzylamine, 8.6 mg (0.045 mmol) of copper (I) iodide, 4.1 mg (0.018 mmol) of palladium acetate and 9.5 mg (0.036 mmol) of triphenylphosphine, and further, 0.18 ml (1.8 mmol) of n-butylamine and 0.135 ml (1. 08 mmol) of tert-butylacetylene under ice cooling. The mixture was stirred for 24 hours at room temperature, and concentrated under reduced pressure. The residue was subjected to silica gel chromatography (n-hexane→n-hexane/ethyl acetate=9/1). The desired fractions were put together and concentrated under reduced pressure to obtain 340 mg (yield: 85%) of the above identified compound as an oily free amine.

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. concentrationconcentrated under reduced pressure
  3. customto obtain 340 mg (yield: 85%) of the

Quellen und Nachweise

ORD-Eintrag
ord-7bc3168c7eac492bb959fa072357d251
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05296612

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