Butylamine → HCID 86754763, compound

HRID 1602112Notes

Reaction equation

HRID 1602112 reaction equation
C[Al](C)C.[CH2:5]([NH2:9])[CH2:6][CH2:7][CH3:8].[NH:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[C:11]1/[CH:19]=[CH:20]/[CH:21]=[C:22](\[O:27][CH3:28])/[C:23](OC)=[O:24]>C1(C)C=CC=CC=1.ClCCl>[CH2:5]([NH:9][C:23](=[O:24])/[C:22](/[O:27][CH3:28])=[CH:21]/[CH:20]=[CH:19]/[C:11]1[NH:10][C:18]2[C:13]([CH:12]=1)=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 3

HCID 8007ButylamineHCID 16682925TrimethylaluminumHCID 86754764HCID 86754764, compound

Product 1

HCID 86754763HCID 86754763, compoundYield 47.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
10 °C

Procedure

A 2M solution of trimethylaluminium in toluene (0.4 ml) was added at room temperature under nitrogen to a solution of butylamine (0.04 ml, 0.39 mmol) in dichloromethane (10 ml). Stirring was continued for 30 minutes and methyl (2Z,4E)-5-(2-indolyl)-2-methoxy-2,4-pentadienoate (0.1 g, 0.39 mmol) was added. The solution was refluxed for 5 hours; after cooling to 10° C., the reaction was quenched with 10% HCl and the separated organic layer was washed with a saturated solution of NaHCO3 and water, dried over Na2SO4 and evaporated under vacuum. The solid residue was triturated with isopropyl ether, to give 55 mg (47.3%) of the title compound as a solid, m.p.=185-186° C.

Workup

  1. temperatureThe solution was refluxed for 5 hours
  2. customthe reaction was quenched with 10% HCl
  3. washthe separated organic layer was washed with a saturated solution of NaHCO3 and water
  4. dry with materialdried over Na2SO4
  5. customevaporated under vacuum
  6. customThe solid residue was triturated with isopropyl ether

Sources & evidence

ORD record
ord-8caa8ea5707940369a327c8f9f484c38
Source dataset
uspto-grants-1999_11
Patent number
US05981525

Reaction notes

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