Sodium Carbonate → HCID 68311086, compound

HRID 470717Notes

Reaction equation

HRID 470717 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:3][CH2:2]1.[N:15]1([CH:24](N2N=C3C=CC=CC3=N2)[NH2:25])[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]=[N:16]1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[N:15]1([C:24](=[NH:25])[N:1]2[CH2:2][CH2:3][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12])[CH2:5][CH2:6]2)[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]=[N:16]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 7238334-(N-Boc-amino)piperidineHCID 70871847HCID 70871847, compound

Product 1

HCID 68311086HCID 68311086, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A dichloromethane (50 ml) solution of tert-butyl piperidin-4-ylcarbamate (7.50 g, 37.9 mmol) was added dropwise to a dichloromethane (150 ml) solution of 1-(1H-benzotriazol-1-yl)-1-(2H-benzotriazol-2-yl)methanamine (J. Org. Chem. 2000, 65, 8080; and J. Org. Chem. 2003, 68, 4941) (10.0 g, 37.9 mmol) and the resulting mixture was stirred at room temperature for 3 days. 10% Aqueous sodium carbonate solution was added to the reaction mixture, followed by extraction with dichloromethane. The organic layer was washed with brine and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give 10.6 g (81%) of the title compound as an oil.

Workup

  1. extractionfollowed by extraction with dichloromethane
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-4e440e450fdd457dbfdd574ae3dfd2ba
Source dataset
uspto-grants-2014_01
Patent number
US08629133B2

Reaction notes

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