2-Methoxybenzoic acid → Tert-Butyl 3-{[(2-methoxy benzoyl)amino]methyl}piperidine-1-carboxylate

HRID 383891Notes

Reaction equation

HRID 383891 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:25][CH2:26][CH:27]1[CH2:32][CH2:31][CH2:30][N:29]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:28]1.[CH3:40][O:41][C:42]1[CH:50]=[CH:49][CH:48]=[CH:47][C:43]=1[C:44](O)=[O:45].C(N(C(C)C)CC)(C)C>C(OCC)(=O)C.CN(C=O)C>[CH3:40][O:41][C:42]1[CH:50]=[CH:49][CH:48]=[CH:47][C:43]=1[C:44]([NH:25][CH2:26][CH:27]1[CH2:32][CH2:31][CH2:30][N:29]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:28]1)=[O:45]

Participants

7

Reactant 4

HCID 113702-Methoxybenzoic acidHCID 81531DiisopropylethylamineHCID 27564831-Boc-3-(aminomethyl)piperidineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 86649438Tert-Butyl 3-{[(2-methoxy benzoyl)amino]methyl}piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

HATU (293 mg, 0.77 mmol) was added to a DMF (3 mL) solution of the compound (150 mg, 0.7 mmol) synthesized in (2), 2-methoxybenzoic acid (117 mg, 0.77 mmol), and diisopropylethylamine (0.27 mL, 1.54 mmol), and the mixture was stirred at room temperature for 24 hours. After adding ethyl acetate, the reaction mixture was washed twice with distilled water, and once with saturated brine. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was then purified using silica gel column chromatography to obtain the target (244 mg, 100%).

Workup

  1. washthe reaction mixture was washed twice with distilled water
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was then purified
  5. customto obtain the target (244 mg, 100%)

Sources & evidence

ORD record
ord-3c51d6329d4b4aeeb90928349085ffaa
Source dataset
uspto-grants-2013_02
Patent number
US08367698B2

Reaction notes

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