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

HRID 1708676Notes

Reaction equation

HRID 1708676 reaction equation
Cl/[CH:2]=[CH:3]/[CH2:4][N:5]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([OH:16])[CH:11]=1)[CH2:6][CH2:7][CH3:8].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N)CCC.[C:41]([C:45]#[CH:46])([CH3:44])([CH3:43])[CH3:42]>[Cu]I.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O1CCCC1>[CH3:42][C:41]([CH3:44])([CH3:43])[C:45]#[C:46]/[CH:2]=[CH:3]/[CH2:4][N:5]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([OH:16])[CH:11]=1)[CH2:6][CH2:7][CH3:8]

Participants

8

Reactant 4

HCID 8007ButylamineHCID 11776TriphenylphosphineHCID 135123,3-Dimethyl-1-butyneHCID 15290084(E)-N-(3-Chloro-2-propenyl)-N-propyl-3-hydroxybenzylamine

Product 1

HCID 15290087(E)-N-(6,6-Dimethyl-2-hepten-4-ynyl)-N-propyl-3-hydroxybenzylamineYield 89%

Reagents, catalysts & solvents 3

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

Procedure

To 12.5 ml of tetrahydrofuran were added 2.00 g (8.34 mmol) of (E)-N-(3-chloro-2-propenyl)-N-propyl-3-hydroxybenzylamine, 79.4 mg (0.417 mmol) of copper (I) iodide, 37.4 mg (0.167 mmol) of palladium acetate and 87.5 mg (0.334 mmol) of triphenylphosphine, and further, 1.65 ml (16.7 mmol) of n-butylamine and 1.23 ml (10.0 mmol) of tert-butylacetylene under ice cooling. The mixture was stirred for 20 hours at room temperature, and concentrated under reduced pressure. The residue was subjected to silica gel chromatography (n-hexane→n-hexane/ethyl acetate=19/1→9/1). 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 2.13 g (yield: 89%) of the above identified compound as slightly yellow crystalline powder.

Workup

  1. concentrationconcentrated 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 2.13 g (yield: 89%) of the

Sources & evidence

ORD record
ord-298102ac9cf34dfb93e54e06cdedfa76
Source dataset
uspto-grants-1994_10
Patent number
US05359091

Reaction notes

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