Butylamine → HCID 15290088, compound

HRID 484537Notes

Reaction equation

HRID 484537 reaction equation
[CH2:1]([NH:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([OH:11])[CH:6]=1)[CH3:2].[C:12]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:13]=1.[CH2:31](N)CCC.[CH3:36][C:37]([OH:41])([CH3:40])[C:38]#[CH:39]>[Cu]I.[Pd](Cl)Cl.O1CCCC1>[OH:41][C:37]([CH3:40])([CH3:36])[C:38]#[C:39]/[CH:31]=[CH:2]/[CH2:1][N:3]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([OH:11])[CH:6]=1)[CH2:12][CH3:13]

Participants

8

Reactant 4

HCID 8007ButylamineHCID 82582-Methyl-3-butyn-2-olHCID 11776TriphenylphosphineHCID 100576883-((Ethylamino)methyl)phenol

Product 1

HCID 15290088HCID 15290088, compoundYield 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-ca119d25906048eb81e9d0a230020f6e
Source dataset
uspto-grants-1993_07
Patent number
US05231183

Reaction notes

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