2-Amino-N-(4-sec-butylphenyl)benzamide → HCID 46842008, compound

HRID 1846355Notes

Reaction equation

HRID 1846355 reaction equation
[NH2:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]([CH2:15][CH3:16])[CH3:14])=[CH:9][CH:8]=1)=[O:5].O1CCCCC1[O:27][CH2:28][C:29]1[CH:36]=[CH:35][C:32]([CH:33]=O)=[CH:31][N:30]=1>CCO>[CH:13]([C:10]1[CH:11]=[CH:12][C:7]([N:6]2[C:4](=[O:5])[C:3]3[C:2](=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:1]=[C:33]2[C:32]2[CH:31]=[N:30][C:29]([CH2:28][OH:27])=[CH:36][CH:35]=2)=[CH:8][CH:9]=1)([CH2:15][CH3:16])[CH3:14]

Participants

4

Reactant 2

HCID 167700372-Amino-N-(4-sec-butylphenyl)benzamideHCID 86659816HCID 86659816, compound

Product 1

HCID 46842008HCID 46842008, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-amino-N-(4-sec-butylphenyl)benzamide (0.250 g, 0.92 mmol) and 6-((tetrahydro-2H-pyran-2-yloxy)methyl)nicotinaldehyde (0.77 mmol) were mixed in anyhydrous EtOH (40 mL) and anyhydrous CuCl2 (0.310 g, 2.3 mmol) was added. After heating at reflux for 1.5 hours, and concentrating, ethyl acetate (150 mL) was added, the mixture was washed with water (2×125 mL), dried (MgSO4), filtered, and concentrated. Flash chromatograph on silica gel, eluting with 50% ethyl acetate/heptane to 100% ethyl acetate, plus re-chromatographing with 30% ethyl acetate/CH2Cl2 to 100% ethyl acetate, afforded the title compound as a white solid (40%). 1H-NMR (300 MHz, DMSO-6): δ8.47 (d, J=1.6 Hz, 1H), 8.21 (d, J=7.8 Hz, 1H), 7.89-7.94 (m, 1H), 7.79 (d, J=7.9 Hz, 1H), 7.60-7.72 (m, 2H), 7.26-7.29 (m, 3H), 7.14-7.18 (m, 2H), 5.42 (t, J=5.8 Hz, 1H), 4.45 (d, J=5.7 Hz, 2H), 2.55-2.64 (m, 1H), 1.37-1.58 (m, 2H), 1.15 (d, J=6.9 Hz, 3H), 0.64 (t, J=7.3 Hz, 3H). MS (APCI) m/z: 386 (M+H)+.

Workup

  1. temperatureAfter heating
  2. temperatureat reflux for 1.5 hours
  3. concentrationconcentrating
  4. additionethyl acetate (150 mL) was added
  5. washthe mixture was washed with water (2×125 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. washFlash chromatograph on silica gel, eluting with 50% ethyl acetate/heptane to 100% ethyl acetate

Sources & evidence

ORD record
ord-3cc18d9971814da284d59ae37c451194
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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