Propargyl alcohol → 3-[3-(Aminomethyl)phenyl]-2-propyn-1-ol

HRID 1169879Notes

Reaction equation

HRID 1169879 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][NH2:6].[CH2:10]([OH:13])[C:11]#[CH:12]>C(NCC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[OH:13][CH2:10][C:11]#[C:12][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][NH2:6]

Participants

5

Reactant 2

HCID 7859Propargyl alcoholHCID 970123-Iodobenzylamine

Product 1

HCID 113671703-[3-(Aminomethyl)phenyl]-2-propyn-1-olYield 90.1%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8021DiethylamineSolvent2×

Procedure

Cuprous iodide (1.06 mg, 0.0056 mmol) was added to a mixture of (PPh3)2PdCl2 (7.84 mg, 0.011 mmol) and 3-iodobenzylamine (262 mg, 1.12 mmol) in dry diethylamine (7 mL) under a nitrogen atmosphere. Then a solution of propargyl alcohol (41.2 μL, 0.73 mmol) in dry diethylamine (3 mL) was added. The resulting solution was stirred at room temperature for 3 h. The solvent was concentrated in vacuo and the residue was partitioned between water (20 mL) and CHCl3 (20 mL). The aqueous phase was separated and extracted with CHCl3 (20 mL×2). The combined organic phases were dried over Na2SO4, filtered and concentrated. The residue was purified by PTLC (chloroform/methanol 9:1) to give 72 (106 mg, 90% yield). 1H NMR (CDCl3, 300 MHz) δ 7.39-7.26 (m, 4H), 4.48 (s, 2H), 3.85 (s, 2H), 1.73 (br s,22H). MS (m/e) (positive FAB) 162.1 (M+H)+.

Workup

  1. concentrationThe solvent was concentrated in vacuo
  2. customthe residue was partitioned between water (20 mL) and CHCl3 (20 mL)
  3. customThe aqueous phase was separated
  4. extractionextracted with CHCl3 (20 mL×2)
  5. dry with materialThe combined organic phases were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by PTLC (chloroform/methanol 9:1)

Sources & evidence

ORD record
ord-a5123c00f53645cba40a77d39f0e418e
Source dataset
uspto-grants-2010_11
Patent number
US07825126B2

Reaction notes

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