Triethylamine → HCID 66750880, compound

HRID 534931Notes

Reaction equation

HRID 534931 reaction equation
Cl.Cl.[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)([CH3:6])([CH3:5])[CH3:4].[CH3:19][O:20][C:21]([C:23]1([C:26](O)=[O:27])[CH2:25][CH2:24]1)=[O:22].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>C(#N)C>[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[CH2:18][CH2:17][N:16]([C:26]([C:23]2([C:21]([O:20][CH3:19])=[O:22])[CH2:25][CH2:24]2)=[O:27])[CH2:15][CH2:14]1)([CH3:6])([CH3:4])[CH3:5]

Participants

8

Reactant 6

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 138618231-(Methoxycarbonyl)cyclopropane-1-carboxylic acidHCID 667511491-(2-Tert-butylphenyl)piperazine dihydrochloride

Product 1

HCID 66750880HCID 66750880, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 1-(2-tert-butylphenyl)piperazine dihydrochloride (Reference Example 1, 0.500 g, 1.72 mmol), 1-(methoxycarbonyl)cyclopropanecarboxylic acid (0.297 g, 2.06 mmol), EDCI (0.395 g, 2.06 mmol), HOBt (0.278 g, 2.06 mmol) and triethylamine (719 μl, 5.16 mmol) in acetonitrile (10 mL) was stirred at room temperature for 16 h. The reaction mixture was poured into saturated sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic layer was washed with saturated sodium hydrogen carbonate solution and brine, dried over MgSO4, and the solvent was evaporated under reduced pressure to give the crude product. The product was purified by flash column chromatography (silica gel, n-hexane/ethyl acetate=90:10 to 65:35) to provide methyl 1-{[4-(2-tert-butylphenyl)piperazin-1-yl]carbonyl}cyclopropanecarboxylate (0.485 g, 82%) as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated sodium hydrogen carbonate solution and brine
  3. dry with materialdried over MgSO4
  4. customthe solvent was evaporated under reduced pressure
  5. customto give the crude product
  6. customThe product was purified by flash column chromatography (silica gel, n-hexane/ethyl acetate=90:10 to 65:35)

Sources & evidence

ORD record
ord-bbad7d05c5664890bbfafbc3692d0b7f
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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