Potassium Carbonate → HCID 67316071, compound

HRID 1012582Notes

Reaction equation

HRID 1012582 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].COC1CCCC1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:36][C:37]([O:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[O:38]>C(=O)(O)[O-].[Na+]>[C:37]([O:39][CH:40]([N:9]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([C:15]#[N:16])=[CH:17][CH:18]=1)[CH2:8][CH2:7][CH2:6][CH2:5][N:4]([CH2:1][CH2:2][CH3:3])[CH2:19][CH2:20][CH3:21])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)(=[O:38])[CH3:36]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 62576Benzyl bromoacetateHCID 138539Cyclopentyl methyl etherHCID 15965417HCID 15965417, compound

Product 1

HCID 67316071HCID 67316071, compoundYield 18.3%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

In a 50 ml recovery flask, 0.462 g (1.61 mmol, 1.0 equivalent) of 4-[(4-dipropylaminobutyl)amino]methylbenzonitrile (2a) and 9.2 ml of cyclopentyl methyl ether were charged and dissolved under a nitrogen stream. After the addition of 0.666 g (4.82 mmol, 3.0 equivalents) of potassium carbonate and 0.736 g (3.21 mmol, 2.0 equivalents) of benzyl bromoacetate at room temperature, 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 100 ml of a saturated sodium bicarbonate aqueous solution, and was extracted twice with 100 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, n-hexane:ethyl acetate=4:1), thereby obtaining 0.128 g of [(4-cyanobenzyl)-(4-dipropylaminobutyl)amino]benzyl acetate (20) as a light yellow oily substance (yield: 18.3%). [HPLC: 97.8% (HPLC measurement conditions A)]

Workup

  1. dissolutiondissolved under a nitrogen stream
  2. extractionwas extracted twice with 100 ml of chloroform
  3. washThe chloroform layer was washed with 100 ml of a saturated sodium chloride aqueous solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. custompurified by silica gel column chromatography (Chromatorex NH, n-hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-b795840d90b343119a44441791b8fa67
Source dataset
uspto-grants-2011_07
Patent number
US07977512B2

Reaction notes

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