Triethylamine → HCID 66751357, compound

HRID 535020Notes

Reaction equation

HRID 535020 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].[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][CH:29]([CH2:32][O:33][C:34]2[CH:42]=[CH:41][C:37]([C:38](O)=[O:39])=[CH:36][CH:35]=2)[CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20].C(N(CC)CC)C.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C)C=O.O>[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:38]([C:37]2[CH:36]=[CH:35][C:34]([O:33][CH2:32][CH:29]3[CH2:28][CH2:27][N:26]([C:24]([O:23][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:25])[CH2:31][CH2:30]3)=[CH:42][CH:41]=2)=[O:39])[CH2:15][CH2:14]1)([CH3:6])([CH3:4])[CH3:5]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 66590087HCID 66590087, compoundHCID 667511491-(2-Tert-butylphenyl)piperazine dihydrochloride

Product 1

HCID 66751357HCID 66751357, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(2-tert-butylphenyl)piperazine dihydrochloride obtained in Reference Example 1 (1.0 g, 3.43 mmol), 4-{[1-(tert-butoxycarbonyl)piperidin-4-yl]methoxy}benzoic acid (1.41 g, 4.2 mmol), triethylamine (1.53 mL, 11.0 mmol), EDCI (0.824 g, 4.3 mmol) and HOBt (0.659 g, 4.3 mmol) in N,N-dimethylformamide (10 mL) was stirred at room temperature for 16 h. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to purify the residue by NH-silica gel column chromatography (hexane/ethyl acetate 10:90 to 0:100). Solvent was removed to obtain a solid (1.6 g, 87%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto purify the residue by NH-silica gel column chromatography (hexane/ethyl acetate 10:90 to 0:100)
  7. customSolvent was removed

Sources & evidence

ORD record
ord-370587b5cf014ec3adba6ce520da5b46
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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