Sodium Hydroxide → HCID 15888084, compound

HRID 636309Notes

Reaction equation

HRID 636309 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]2[CH2:21][CH:20]([CH2:22][C:23]([O:25]CC)=[O:24])[C:19]3[CH:28]=[CH:29][CH:30]=[CH:31][C:18]=3[CH2:17][C:16]=2[CH:32]=1.[OH-].[Na+]>CCO>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]2[CH2:21][CH:20]([CH2:22][C:23]([OH:25])=[O:24])[C:19]3[CH:28]=[CH:29][CH:30]=[CH:31][C:18]=3[CH2:17][C:16]=2[CH:32]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15434951HCID 15434951, compound

Product 1

HCID 15888084HCID 15888084, compoundYield 79.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl (±)-10,11-dihydro-3-[3-(2-pyridylamino)-1-propyloxy]-5H-dibenzo[a,d]cycloheptene-10-acetate (0.94 g, 2.18 mmole) and 1.0 N NaOH (2.6 mL, 2.62 mmole) in absolute EtOH (19.2 mL) is warmed in an oil bath set at 50° C. After 28.5 hr, the reaction was concentrated on the rotavap and the residue was purified by ODS chromatography (1:1 MeOH/H2O). Concentration left a cloudy, aqueous solution, which was made homogeneous by addition of a little 1.0 N NaOH. The pH was adjusted to 7 with 1.0 N HCl, and the solid precipitate was collected and washed with H2O. The mother liquors were concentrated, and the residue treated similarly to afford a small second crop. The combined materials were dried in high vacuum at 40° C. to afford the title compound (0.70g, 79%) as a nearly colorless solid: HPLC (Hamilton PRP-1®, 40% CH3CN/H2O containing 0.1% TFA) k′=1.2; 1H NMR (400 MHz, DMSO-d6) δ 7.94 (d, J=4.4 Hz, 1H), 7.32-7.41 (m, 1H), 7.03-7.22 (m, 4H), 6.97 (d, J=8.4 Hz, 1H), 6.83 (d, J=2.4 Hz, 1H), 6.60-6.74 (m, 2H), 6.41-6.50 (m, 2H), 4.20 (d, J=14.7 Hz, 1H), 4.00 (t, J=6.2 Hz, 2H), 3.88 (d, J=14.7 Hz, 1H), 3.60-3.70 (m, 1H), 3.26-3.40 (m, 2H, partially obscured by residual solvent signal), 3.20 (dd, J=15.1, 4.3 Hz, 1H), 2.83 (dd, J=15.1, 10.3 Hz, 1H), 2.60 (dd, J=15.9, 5.3 Hz, 1H), 2.50 (dd, 1H, partially obscured by residual solvent signal), 1.88-2.00 (m, 2H); MS (ES) m/e 403 (M+H)+. Anal. Calcd for C25H26N2O3 .0.25 H2O: C, 73.78; H, 6.56; N, 6.88. Found: C, 73.85; H, 6.47; N, 6.75.

Workup

  1. temperatureis warmed in an oil bath
  2. customset at 50° C
  3. concentrationthe reaction was concentrated on the rotavap
  4. customthe residue was purified by ODS chromatography (1:1 MeOH/H2O)
  5. concentrationConcentration
  6. waitleft a cloudy, aqueous solution, which
  7. additionwas made homogeneous by addition of a little 1.0 N NaOH
  8. customthe solid precipitate was collected
  9. washwashed with H2O
  10. concentrationThe mother liquors were concentrated
  11. additionthe residue treated similarly
  12. customto afford a small second crop
  13. customThe combined materials were dried in high vacuum at 40° C.

Sources & evidence

ORD record
ord-b58b7954b5554ea29a7e31adebd8df11
Source dataset
uspto-grants-2001_02
Patent number
US06191304B1

Reaction notes

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