Butylamine → (E)-N-(6,6-Dimethyl-2-hepten-4-ynyl)-N-ethyl-3-hydroxybenzylamine

HRID 487782Notes

Reaction equation

HRID 487782 reaction equation
Cl/[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].C(N)CCC.[C:21]([C:25]#[CH:26])([CH3:24])([CH3:23])[CH3:22]>[Cu]I.O1CCCC1>[CH3:22][C:21]([CH3:24])([CH3:23])[C:25]#[C:26]/[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

6

Reactant 3

HCID 8007ButylamineHCID 135123,3-Dimethyl-1-butyneHCID 10376384(E)-N-(3-Chloro-2-propenyl)-N-ethyl-3-hydroxybenzylamine

Product 1

HCID 10445905(E)-N-(6,6-Dimethyl-2-hepten-4-ynyl)-N-ethyl-3-hydroxybenzylamineYield 77%

Reagents, catalysts & solvents 2

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

Procedure

To 30 ml of tetrahydrofuran were added 4.51 g (20 mmol) of (E)-N-(3-chloro-2-propenyl)-N-ethyl-3-hydroxybenzylamine, 190.5 mg (1 mmol) of copper (I) iodide and 324 mg (0.28 mmol) of tetrakis (triphenylphosphine)palladium, and further, 3.95 ml (40 mmol) of n-butylamine and 2.94 ml (24 mmol) of tert-butylacetylene 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=7/3). The desired fractions were put together and concentrated under reduced pressure to oil. The oil was cooled to crystallize and the crystals were suspended in cooled n-hexane. The crystals were collected by filtration and then dried to obtain 4.20 g (yield: 77%) of the above identified compound as slightly yellow crystalline powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. concentrationconcentrated under reduced pressure to oil
  3. temperatureThe oil was cooled
  4. customto crystallize
  5. filtrationThe crystals were collected by filtration
  6. customdried
  7. customto obtain 4.20 g (yield: 77%) of the

Sources & evidence

ORD record
ord-1faf8697994e47989e2dfb54ba204901
Source dataset
uspto-grants-1994_03
Patent number
US05296612

Reaction notes

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