Butylamine → HCID 11024104, compound

HRID 1648618Notes

Reaction equation

HRID 1648618 reaction equation
Cl/[CH:2]=[CH:3]/[CH2:4][N:5]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Br: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.[C:40]([C:44]#[CH:45])([CH3:43])([CH3:42])[CH3:41]>[Cu]I.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O1CCCC1>[CH3:41][C:40]([CH3:43])([CH3:42])[C:44]#[C:45]/[CH:2]=[CH:3]/[CH2:4][N:5]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Br:15])[CH:10]=1)[CH2:6][CH3:7]

Participants

8

Reactant 4

HCID 8007ButylamineHCID 11776TriphenylphosphineHCID 135123,3-Dimethyl-1-butyneHCID 15290085HCID 15290085, compound

Product 1

HCID 11024104HCID 11024104, compoundYield 82%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To 10 ml tetrahydrofuran were added 1.44 g (5 mmol) of (E)-N-(3-chloro-2-propenyl)-N-ethyl-3-bromobenzylamine, 47.6 mg (0.25 mmol) of copper (I) iodide and 22.4 mg (0.1 mmol) of palladium acetate and 52.5 mg (0.2 mmol) of triphenylphosphine, and further, 1.0 ml (10 mmol) of n-butylamine and 0.74 ml (6 mmol) of tert-butylacetylene under ice cooling. The mixture was stirred for 20 hours at room temperature, and concentrated under reduced oressure. The residue was subjected to silica gel chromatography (n-hexane→n-hexane/ethyl acetate =20/1). The desired fractions were put together and concentrated under reduced pressure to obtain 1.37 g (yield: 82% ) of the above identified compound as an oil.

Workup

  1. concentrationconcentrated under reduced oressure
  2. concentrationconcentrated under reduced pressure
  3. customto obtain 1.37 g (yield: 82% ) of the

Sources & evidence

ORD record
ord-6ae187da8c5d4fcdb97bfc3416f4a7c2
Source dataset
uspto-grants-1995_07
Patent number
US05436354

Reaction notes

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