Pyrrole-2-carboxaldehyde → HCID 16117424, compound

HRID 1012580Notes

Reaction equation

HRID 1012580 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].[NH:22]1[CH:26]=[CH:25][CH:24]=[C:23]1[CH:27]=O.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)[CH2:27][C:23]1[NH:22][CH:26]=[CH:25][CH:24]=1)[CH2:20][CH3:21]

Participants

6

Reactant 4

HCID 13854Pyrrole-2-carboxaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 15965417HCID 15965417, compound

Product 1

HCID 16117424HCID 16117424, compoundYield 54.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

0.492 g (1.71 mmol) of 4-[(4-dipropylaminobutyl)amino]methylbenzonitrile (2a), 9.8 ml of ethanol, and 0.325 g (3.42 mmol, 2.0 equivalents) of pyrrole-2-aldehyde were charged in a 50 ml recovery flask under a nitrogen stream. The mixture was then cooled to 0° C. After the addition of 0.870 g (4.11 mmol, 2.4 equivalents) of sodium triacetoxyborohydride, the mixture was stirred at room temperature for 17 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=1:1), thereby obtaining 0.342 g of 4-{[(4-dipropylaminobutyl)-(1H-pyrrol-2-ylmethyl)amino]methyl}benzonitrile (18) as a light yellow oily substance (yield: 54.5%). [HPLC: 87.6% (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=1:1)

Sources & evidence

ORD record
ord-4fb2a3bd60fe4e02be9b2aefc0da91ab
Source dataset
uspto-grants-2011_07
Patent number
US07977512B2

Reaction notes

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