Triethylamine → HCID 46911245, compound

HRID 538009Notes

Reaction equation

HRID 538009 reaction equation
Cl[C:2](OC1C=CC([N+]([O-])=O)=CC=1)=[O:3].[OH:14][CH:15]1[CH2:20][CH2:19][N:18]([C:21]2[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=2)[CH2:17][CH2:16]1.Cl.[CH3:29][N:30]1[CH:34]=[CH:33][CH:32]=[C:31]1[C:35]([N:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1)=[O:36].C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>O1CCCC1>[OH:14][CH:15]1[CH2:20][CH2:19][N:18]([C:21]2[CH:26]=[CH:25][C:24]([NH:27][C:2]([N:40]3[CH2:39][CH2:38][N:37]([C:35]([C:31]4[N:30]([CH3:29])[CH:34]=[CH:33][CH:32]=4)=[O:36])[CH2:42][CH2:41]3)=[O:3])=[CH:23][CH:22]=2)[CH2:17][CH2:16]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 516892Sodium BicarbonateHCID 167921071-(4-Aminophenyl)piperidin-4-olHCID 66584372HCID 66584372, compound

Product 1

HCID 46911245HCID 46911245, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4-nitrophenyl chloroformate (242 mg, 1.2 mmol) was dissolved in tetrahydrofuran (3 ml), and a tetrahydrofuran (4 ml) solution of the 4-hydroxy-N-(4-aminophenyl)piperidine (211 mg, 1.0 mmol) obtained in Example 1(2) was added dropwise at −30° C. After stirring for 30 minutes at the same temperature, 1-[(1-methyl-1H-pyrrol-2-yl)carbonyl]piperazine hydrochloride (252 mg, 1.1 mmol) and triethylamine (0.49 ml, 3.5 mmol) were added to the mixture, followed by stirring at room temperature for 17 hours. A saturated sodium bicarbonate aqueous solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated sodium chloride, and dried over anhydrous sodium sulfate. After the desiccant was filtered off, the residue obtained by evaporation under reduced pressure was purified using medium pressure silica gel flash column chromatography (NH silica gel, methanol:chloroform=0:1 to 1:50), thereby obtaining N-(4-(4-hydroxypiperidin-1-yl)-phenyl)-4-((1-methylpyrrol-2-yl)-carbonyl)-1-piperazinecarboxamide (256 mg, 62%) as a milky-white solid.

Workup

  1. additionwere added to the mixture
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with water and saturated sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter the desiccant was filtered off
  6. customthe residue obtained by evaporation under reduced pressure
  7. customwas purified

Sources & evidence

ORD record
ord-b13bc68b0b8b440f8c1db8f40346fb9f
Source dataset
uspto-grants-2014_10
Patent number
US08865714B2

Reaction notes

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