5-Methylfurfural → HCID 16117297, compound

HRID 1012579Notes

Reaction equation

HRID 1012579 reaction equation
[CH2:1]([N:4]([CH2:19][CH2:20][CH3:21])[CH2:5][CH2:6][CH2:7][CH2:8][NH:9][CH2:10][C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=1)[CH2:2][CH3:3].[CH3:22][C:23]1[O:27][C:26]([CH:28]=O)=[CH:25][CH:24]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(O)C>[CH2:19]([N:4]([CH2:1][CH2:2][CH3:3])[CH2:5][CH2:6][CH2:7][CH2:8][N:9]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([C:15]#[N:16])=[CH:17][CH:18]=1)[CH2:28][C:26]1[O:27][C:23]([CH3:22])=[CH:24][CH:25]=1)[CH2:20][CH3:21]

Participants

6

Reactant 4

HCID 120975-MethylfurfuralHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 15965417HCID 15965417, compound

Product 1

HCID 16117297HCID 16117297, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

0.485 g (1.69 mmol) of 4-[(4-dipropylaminobutyl)amino]methylbenzonitrile (2a), 9.7 ml of ethanol, and 371 mg (3.37 mmol, 2.0 equivalents) of 5-methyl-2-furaldehyde were charged in a 50 ml recovery flask under a nitrogen stream. The mixture was then cooled to 0° C. After the addition of 0.857 g (4.05 mmol, 2.4 equivalents) of sodium triacetoxyborohydride, the mixture was stirred at room temperature for 19 hours. After confirming the disappearance of the raw material by TLC, the reaction solution was added to 50 ml of a saturated sodium bicarbonate aqueous solution, and extracted twice with 50 ml of chloroform. The chloroform layer was washed with 100 ml of a saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate, concentrated, and purified by silica gel column chromatography (Chromatorex NH, chloroform:n-hexane=11:1), thereby obtaining 0.640 g of 4-{[(4-dipropylaminobutyl)-(5-methylfuran-2-ylmethyl)amino]methyl}benzonitrile (17) as a light yellow oily substance (yield: 99.5%). [HPLC: 98.9% (HPLC measurement conditions B)]

Workup

  1. extractionextracted twice with 50 ml of chloroform
  2. washThe chloroform layer was washed with 100 ml of a saturated sodium chloride aqueous solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. custompurified by silica gel column chromatography (Chromatorex NH, chloroform:n-hexane=11:1)

Sources & evidence

ORD record
ord-4f20e355d25349c18c280358828a1c54
Source dataset
uspto-grants-2011_07
Patent number
US07977512B2

Reaction notes

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