Triethylamine → 3-(4-Chlorophenyl)allylamine

HRID 597873Notes

Reaction equation

HRID 597873 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][CH2:10][NH2:11])=[CH:4][CH:3]=1.CCN(CC)CC>CO.C(Cl)Cl.[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].CO.ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]=[CH:9][CH2:10][NH2:11])=[CH:6][CH:7]=1

Participants

7

Reactant 2

HCID 8471TriethylamineHCID 589523443-(4-Chlorophenyl)prop-2-yn-1-amine

Product 1

HCID 536960003-(4-Chlorophenyl)allylamineYield 74.1%

Reagents, catalysts & solvents 4

HCID 131709914Lindlars catalystCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of 3-(4-chloro-phenyl)-prop-2-ynylamine (14.0 g) in 200 mL each of MeOH and CH2Cl2 was added Et3N (1.2 mL) and Lindlar catalyst (1.4 g) and the resulting suspension was stirred under a H2 balloon. The reaction was followed by TLC (i.e., thin layer chromatography) using 6% methanol-dichloromethane as eluent and once completed, filtered through a CELITE pad, concentrated and purified by chromatography to provide 10.5 g of 3-(4-chloro-phenyl)-allylamine. MS: m/e 168.6 (MH+)

Workup

  1. filtrationfiltered through a CELITE pad
  2. concentrationconcentrated
  3. custompurified by chromatography

Sources & evidence

ORD record
ord-f6677543d679486aaec74150fd376173
Source dataset
uspto-grants-2011_03
Patent number
US07897601B2

Reaction notes

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