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Sodium Carbonate → Tert-butyl 4-((2-(pyridin-4-yl)ethyl)carbamoyl)piperidine-1-carboxylate

HRID 83654
Notes
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Reaction equation

HRID 83654 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC[N:19]([CH:23]([CH3:25])C)[CH:20]([CH3:22])C.C1C=[CH:28][C:29]2N(O)N=[N:32][C:30]=2C=1.N1C=CC=CC=1CCN.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl.C(Cl)CCl>[N:19]1[CH:20]=[CH:22][C:28]([CH2:29][CH2:30][NH:32][C:14]([CH:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][CH2:12]2)=[O:16])=[CH:25][CH:23]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 10340Sodium CarbonateHCID 757711-HydroxybenzotriazoleHCID 759192-PyridineethanamineHCID 81531DiisopropylethylamineHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acid

Product 1

HCID 68379709Tert-butyl 4-((2-(pyridin-4-yl)ethyl)carbamoyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent2×

Procedure

The following was added to DCM: 1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid (600 mg, 2.62 mmol), DIPEA (1.37 mL, 7.85 mmol), EDC (552 mg, 2.88 mL), HOBT (441 mg, 2.88 mmol), and pyridylethylamine (0.34 mL, 2.88 mL). The solution was stirred at rt for 17 h, at which time the DCM was stripped off and 10% aq. sodium carbonate was added. Material was extracted out with EtOAc (3×). The organic extractions were pooled, dried over magnesium sulfate, and concentrated in vacuo. The residue was taken up in a small amount of EtOAc and diethyl ether was added. The precipitate was collected over a filter and washed with diethyl ether to give the title compound as an off-white solid. (Yield: 634 mg, 1.9 mmol, 73%) 1H NMR (400 MHz, CDCl3) 8.49, 7.09, 5.67-5.54, 4.10, 3.52, 2.81, 2.68, 2.14, 1.81-1.66, 1.56, 1.43

Workup

  1. extractionMaterial was extracted out with EtOAc (3×)
  2. extractionThe organic extractions
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. additionwas added
  6. customThe precipitate was collected over
  7. filtrationa filter
  8. washwashed with diethyl ether

Sources & evidence

ORD record
ord-846faa964a934afb9aae8f248cc6860c
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08846684B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes