3-Carboxybenzaldehyde → HCID 57979992, compound

HRID 446542Notes

Reaction equation

HRID 446542 reaction equation
[C:1]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8](=[O:20])[O:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][NH:18][CH3:19])[CH2:12][CH2:11]1.[CH:27]([C:29]1[CH:30]=[C:31]([CH:35]=[CH:36][CH:37]=1)[C:32](O)=[O:33])=[O:28].CN(C(ON1N=NC2C1=CC=CC=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.C(=O)([O-])O.[Na+]>ClCCl.C(OCC)(=O)C>[C:1]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8](=[O:20])[O:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][N:18]([C:27]([C:29]2[CH:37]=[CH:36][CH:35]=[C:31]([CH:32]=[O:33])[CH:30]=2)=[O:28])[CH3:19])[CH2:12][CH2:11]1

Participants

8

Reactant 5

HCID 120773-CarboxybenzaldehydeHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 566436031-(2-(Methylamino)ethyl)piperidin-4-yl [1,1'-biphenyl]-2-ylcarbamate

Product 1

HCID 57979992HCID 57979992, compoundYield 112.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-[2-(Methylamino)ethyl]piperidin-4-yl biphenyl-2-ylcarbamate (1.00 g, 2.83 mmol) was dissolved in dichloromethane (20 mL), 3-formylbenzoic acid (425 mg, 2.83 mmol), 0-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluroniumhexafluorophosphate (1.08 g, 2.83 mmol) and diisopropylethylamine (1.48 mL, 8.49 mmol) were added under ice cooling, and the mixture was stirred at room temperature under a nitrogen atmosphere for 16 hours. After the reaction was completed, a saturated aqueous sodium hydrogencarbonate solution was added, and ethyl acetate was further added to separate the layers. The resulting organic layer was separated, washed with saturated sodium chloride solution, and then dried with anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate:methanol, 10:1, v/v) to give the title compound (1.54 g; yield, 100%) as a colorless oily substance.

Workup

  1. customto separate the layers
  2. customThe resulting organic layer was separated
  3. washwashed with saturated sodium chloride solution
  4. dry with materialdried with anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by NH silica gel column chromatography (ethyl acetate

Sources & evidence

ORD record
ord-0e4236d21aa44da5bdaa5200beb3eb3c
Source dataset
uspto-grants-2013_07
Patent number
US08476253B2

Reaction notes

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