1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 22013914, compound

HRID 2416944Notes

Reaction equation

HRID 2416944 reaction equation
CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[Br:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([OH:31])=O.[CH:32]([C:35]1[CH:41]=[CH:40][CH:39]=[C:38]([CH:42]([CH3:44])[CH3:43])[C:36]=1[NH2:37])([CH3:34])[CH3:33]>CN(C=O)C>[Br:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([NH:37][C:36]1[C:38]([CH:42]([CH3:43])[CH3:44])=[CH:39][CH:40]=[CH:41][C:35]=1[CH:32]([CH3:34])[CH3:33])=[O:31]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 32484DiisopropylanilineHCID 757711-HydroxybenzotriazoleHCID 1217237-Bromoheptanoic acid

Product 1

HCID 22013914HCID 22013914, compoundYield 30.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2 N Jones' reagent (20 ml) was gradually and dropwise added to an acetone (20 ml) solution of 7-bromoheptanol (1.95 g, 10 mmols) with cooing with ice, and then stirred at room temperature for 10 minutes. The reaction mixture was extracted three times with ether (80 ml). The organic layer was washed with water, and then extracted three times with an aqueous saturated solution of sodium hydrogencarbonate (120 ml). The aqueous layers were combined, then made acidic (pH=1) with 5% sulfuric acid added thereto, and extracted with ethyl acetate. The resulting organic layer was washed with water and saturated saline in that order, and dried with anhydrous sodium sulfate, and the solvent was evaporated. 1.45 g (70%) of 7-bromoheptanoic acid was obtained as colorless needle-like crystals. WSC (891 mg, 4.7 mmols) and HOBt (628 mg, 4.1 mmols) were added to a DMF (20 ml) solution of the resulting carboxylic acid (1.06 g, 5 mmols) and 2,6-diisopropylaniline (738 mg, 4.2 mmols), and stirred at room temperature for 12 hour. The reaction mixture was extracted with ether. The organic layer was washed with water, 1N HCl, an aqueous saturated solution of sodium hydrogencarbonate and saturated saline in that order, and dried with anhydrous magnesium sulfate, and the solvent was evaporated Then, the residue was purified through silica gel colt chromatography (developer:hexane/acetone=5/1), and the resulting crystals ware recrystallized from ether-hexane to obtain 466 mg (yield: 30%) of 7-bromo-N-(2, 6-diisopropylphenyl) heptanamide as colorless needle-like crystals.

Workup

  1. extractionThe reaction mixture was extracted with ether
  2. washThe organic layer was washed with water, 1N HCl
  3. dry with materialan aqueous saturated solution of sodium hydrogencarbonate and saturated saline in that order, and dried with anhydrous magnesium sulfate
  4. customthe solvent was evaporated
  5. customthe residue was purified through silica gel colt chromatography (developer:hexane/acetone=5/1)
  6. customthe resulting crystals ware recrystallized from ether-hexane

Sources & evidence

ORD record
ord-2947a2bca79e4bcda4336c0958ab38bd
Source dataset
uspto-grants-2004_11
Patent number
US06825223B2

Reaction notes

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