1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 131725863, compound

HRID 1792987Notes

Reaction equation

HRID 1792987 reaction equation
[OH:1][C:2]1[C:10]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]CCCC)=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]CCCC.[Cl:31][C:32]1[CH:37]=[CH:36][C:35]([C:38](=[O:46])[CH2:39][N:40]2[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]2)=[CH:34][CH:33]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C([O-])(O)=O.[Na+]>CC#N>[Cl:31][C:32]1[CH:37]=[CH:36][C:35]([C:38](=[O:46])[CH2:39][N:40]2[CH2:41][CH2:42][N:43]([C:6](=[O:8])[C:5]3[CH:4]=[C:3]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:2]([OH:1])=[C:10]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH:9]=3)[CH2:44][CH2:45]2)=[CH:34][CH:33]=1

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 4738722HCID 4738722, compoundHCID 69639848HCID 69639848, compound

Product 1

HCID 131725863HCID 131725863, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 4-hydroxy-3,5-bis-nonyloxy benzoic acid (98 mg, 0.23 mmol), 1-(4-chlorophenyl)-2-piperazine-1-yl-ethanone (111 mg, 0.46 mmol), EDCI (89 mg, 0.46 mmol) and HOBT (63 mg, 0.46 mmol) was added MeCN (3 ml) and stirred for 1 hour at room temperature. The solution was added with NaHCO3 to finish the reaction. The solution was extracted with EtOAc, dried over anhydrous Na2SO4 and filtered. The obtained filterate was vacuum concentrated to give the residue, which was purified by column chromatography (Hexane:EtOAc=1:10), yielding 98 mg (66%) of 1-(4-chlorophenyl)-2-[4-(4-hydroxy-3,5-bis-pentyloxybenzoyl)piperizine -1-yl]ethanone.

Workup

  1. customthe reaction
  2. extractionThe solution was extracted with EtOAc
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give the residue, which
  7. customwas purified by column chromatography (Hexane:EtOAc=1:10)

Sources & evidence

ORD record
ord-87cdbd6209e34c60b3fe63b0dfcb5ba8
Source dataset
uspto-grants-2006_07
Patent number
US07078407B2

Reaction notes

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