2-Benzofurancarboxaldehyde → HCID 59773023, compound

HRID 2220693Notes

Reaction equation

HRID 2220693 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[CH:10]=O.[CH3:12][N:13]1[CH2:17][CH2:16][CH2:15][CH:14]1[CH2:18][CH2:19][NH2:20].[Na]>ClCCl>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[CH2:10][NH:20][CH2:19][CH2:18][CH:14]1[CH2:15][CH2:16][CH2:17][N:13]1[CH3:12]

Participants

5

Reactant 3

HCID 613412-BenzofurancarboxaldehydeHCID 983882-(2-Aminoethyl)-1-methylpyrrolidineHCID 5360545Sodium

Product 1

HCID 59773023HCID 59773023, compoundYield 32.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Experimental condition analogous to Example 5, from 2-benzofurancarboxaldehyde 0.14 g (1.1 mmol), 2-(1-methyl-pyrrolidin-2-yl)-ethylamine 0.14 g (1 mmol), and sodium triacethoxyborohydride 0.31 g (1.5 mmol), in 10 mL Dichloromethane. Purification using silica chromatography, elution with dichloromethane-methanol-ammonium hydroxide, 9-1-0.25, gave 83 mg of compound.

Workup

  1. customPurification
  2. washsilica chromatography, elution with dichloromethane-methanol-ammonium hydroxide, 9-1-0.25

Sources & evidence

ORD record
ord-f8c0f5f0306445f2acc66cd32c3a93f1
Source dataset
uspto-grants-2008_08
Patent number
US07417062B2

Reaction notes

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