3-Phenylpropylamine → HCID 67343242, compound

HRID 1673414Notes

Reaction equation

HRID 1673414 reaction equation
CC(C)([O-])C.[Na+].[C:7]([NH:15][C:16]1[CH:28]=[C:27](I)[CH:26]=[CH:25][C:17]=1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:30]1([CH2:36][CH2:37][CH2:38][NH2:39])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[C:7]([NH:15][C:16]1[CH:28]=[C:27]([NH:39][CH2:38][CH2:37][CH2:36][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:26]=[CH:25][C:17]=1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 162593-PhenylpropylamineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 67342064HCID 67342064, compound

Product 1

HCID 67343242HCID 67343242, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

53 mg of tris(dibenzylideneacetone)dipalladium(0) and 0.17 g sodium tert-butoxide were added to 5 mL of toluene solution containing 0.50 g of tert-butyl 2-(benzamido)-4-iodobenzoate, 0.25 mL of 3-phenylpropylamine and 36 mg of rac-2,2′-bis(diphenylphosphino)-1,1-binaphthyl at room temperature and stirred at 80° C. for 7 hours. After the reaction mixture was cooled to room temperature, insoluble were removed by filtration, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [eluent; hexane:ethyl acetate=6:1] to obtain 0.11 g of tert-butyl 2-(benzamido)-4-(3-phenylpropylamino)benzoate as brown oil.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. custominsoluble were removed by filtration
  3. customthe solvent was evaporated under reduced pressure
  4. customThe obtained residue was purified with silica gel column chromatography [eluent; hexane:ethyl acetate=6:1]

Sources & evidence

ORD record
ord-6deb19e906f3457e84c4bc156172a064
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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