Triethylamine → 4-(4-Hydroxymethylphenylethynyl)benzylamine

HRID 1662926Notes

Reaction equation

HRID 1662926 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH2:9])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH:29][CH2:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]#[CH:38])=[CH:33][CH:32]=1.CCN(CC)CC>C1COCC1.CCOC(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.[Cu]I>[OH:29][CH2:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]#[C:38][C:2]2[CH:7]=[CH:6][C:5]([CH2:8][NH2:9])=[CH:4][CH:3]=2)=[CH:33][CH:32]=1

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 27375334-IodobenzylamineHCID 11170993(4-Ethynylphenyl)methanol

Product 1

HCID 674365394-(4-Hydroxymethylphenylethynyl)benzylamine

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-iodo-(aminomethyl)-benzene (7.4 mmol), palladium acetate (0.015 mmol), triphenylphosphine (0.18 mmol), and CuI (0.18 mmol) in anhydrous THF (40 mL) is thoroughly degassed by purging under Ar. To this solution under Ar is added 4-hydroxymethylphenylacetylene (7.4 mmol) and Et3N (11 mmol). The mixture was then incubated at RT with stirring overnight. The mixture is diluted with EtOAc (150 mL) and the solids are removed by filtration through Celite. The crude residue obtained from the filtrate is purified by flash column chromatography (silica, 1:1 hexane:Et2O) to give the product as a slightly yellow solid.

Workup

  1. customis thoroughly degassed
  2. customby purging under Ar
  3. customwas then incubated at RT
  4. customthe solids are removed by filtration through Celite

Sources & evidence

ORD record
ord-7b19e1b238c547819bf26007f017f348
Source dataset
uspto-grants-2011_10
Patent number
US08034563B1

Reaction notes

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