Butylamine → (E)-N-(6-Hydroxy-6-methyl-2-hepten-4-ynyl)-N-ethyl-3-hydroxybenzylamine

HRID 487785Notes

Reaction equation

HRID 487785 reaction equation
Cl/[C:2](/[CH2:16][CH3:17])=[CH:3]/[CH2:4][N:5]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([OH:15])[CH:10]=1)[CH2:6][CH3:7].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N)CCC.[CH3:42][C:43]([OH:47])(C)[C:44]#C>[Cu]I.[Pd](Cl)Cl.O1CCCC1>[OH:47][C:43]([CH3:44])([CH3:42])[C:17]#[C:16]/[CH:2]=[CH:3]/[CH2:4][N:5]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([OH:15])[CH:10]=1)[CH2:6][CH3:7]

Participants

8

Reactant 4

HCID 8007ButylamineHCID 82582-Methyl-3-butyn-2-olHCID 11776TriphenylphosphineHCID 18653083(E)-N-(3-chloro-2-pentenyl)-N-ethyl-3-hydroxybenzylamine

Product 1

HCID 15290088(E)-N-(6-Hydroxy-6-methyl-2-hepten-4-ynyl)-N-ethyl-3-hydroxybenzylamineYield 78%

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

To 7.5 ml tetrahydrofuran were added 1.13 g (5 mmol) of (E)-N-(3-chloro-2-pentenyl)-N-ethyl-3-hydroxybenzylamine, 4.76 mg (0.25 mmol) of copper (I) iodide, 18.0 mg (0.1 mmol) of palladium chloride and 52.5 mg (0.2 mmol) of triphenylphosphine, and further, 0.99 ml (10 mmol) of n-butylamine and 0.58 ml (6 mmol) of 3-methyl-1-butyne-3-ol under ice cooling. The mixture was stirred for 20 hours at room temperature. The reaction mixture was concentrated under reduced pressure and the residue was subjected to silica gel chromatography (n-hexane→n-hexane/ethyl acetate=3/2). The desired fractions were put together and concentrated under reduced pressure to obtain 1.07 g (yield: 78%) of the above identified compound as an oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. concentrationconcentrated under reduced pressure
  3. customto obtain 1.07 g (yield: 78%) of the

Sources & evidence

ORD record
ord-299fcbd83508414192f0162a2607c88c
Source dataset
uspto-grants-1994_03
Patent number
US05296612

Reaction notes

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