Aniline → HCID 51204633, compound

HRID 1419575Notes

Reaction equation

HRID 1419575 reaction equation
C(N(CC)CC)C.[C:8]([O:12][C:13]([N:15]1[CH2:20][CH2:19][CH:18]([C:21]([OH:23])=O)[CH2:17][CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9].[NH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1>ClCCl>[C:25]1([NH:24][C:21]([CH:18]2[CH2:17][CH2:16][N:15]([C:13]([O:12][C:8]([CH3:9])([CH3:10])[CH3:11])=[O:14])[CH2:20][CH2:19]2)=[O:23])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 6115AnilineHCID 8471TriethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acid

Product 1

HCID 51204633HCID 51204633, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (10.04 mL, 7.28 g, 72 mmol) was added to stirred, cooled (0° C.) mixture of 1-t-butoxycarbonylpiperidine-4-carboxylic acid (6.87 g, 30 mmol), aniline (2.73 mL, 2.79 g, 30 mmol) and bis(2-oxo-3-oxazolidinyl)phosphinic chloride (9.16 g, 36 mmol) in dichloromethane (50 mL) and the mixture was stirred at room temperature for 18 h. The solvent was evaporated under reduced pressure, water (50 mL) was added and the mixture was extracted with ethyl acetate (4×50 mL). The combined organic fractions were washed with aqueous citric acid (10%, 2×50 mL), aqueous sodium hydrogen carbonate (saturated, 2×50 mL) and brine (50 mL), dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with EtOAc/Hexane (40:60) to give the title compound as a colorless foam (7.23 g, 79%), δH (250 MHz, CDCl3) 7.51 (2H, d, J 7.6 Hz), 7.32 (2H, t, J 7.6 Hz), 7.26 (1H, br s), 7.11 (1H, t, J 7.6 Hz), 4.19 (2H, m), 2.78 (2H, m), 2.38 (1H, m), 1.90 (2H, m), 1.77 (2H, m), and 1.47 (9H, s). m/e (ES+) 305 (MH+).

Workup

  1. temperaturecooled
  2. stirringthe mixture was stirred at room temperature for 18 h
  3. customThe solvent was evaporated under reduced pressure, water (50 mL)
  4. additionwas added
  5. extractionthe mixture was extracted with ethyl acetate (4×50 mL)
  6. washThe combined organic fractions were washed with aqueous citric acid (10%, 2×50 mL), aqueous sodium hydrogen carbonate (saturated, 2×50 mL) and brine (50 mL)
  7. dry with materialdried (MgSO4)
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was purified by flash column chromatography on silica gel
  10. washeluting with EtOAc/Hexane (40:60)

Sources & evidence

ORD record
ord-64dae26737954bbb9dd543b98b81d1e4
Source dataset
uspto-grants-1999_03
Patent number
US05885999

Reaction notes

Loading…