Hydrochloric Acid → HCID 18518277, compound

HRID 1369260Notes

Reaction equation

HRID 1369260 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:14]=[CH:15][C:16]3[CH2:22][CH:21]([CH2:23][C:24]([O:26]CC)=[O:25])[C:20]4[CH:29]=[CH:30][CH:31]=[CH:32][C:19]=4[O:18][C:17]=3[CH:33]=2)[CH:3]=1.[OH-].[Na+].Cl>CCO>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:14]=[CH:15][C:16]3[CH2:22][CH:21]([CH2:23][C:24]([OH:26])=[O:25])[C:20]4[CH:29]=[CH:30][CH:31]=[CH:32][C:19]=4[O:18][C:17]=3[CH:33]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86585480HCID 86585480, compound

Product 1

HCID 18518277HCID 18518277, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl (±)-10,11-dihydro-3-[3-(4-methylpyridin-2-ylamino)-1-propyloxy]dibenzo[b,f]oxepine-10-acetate (119 mg, 0.27 mmole) and 0.991 N NaOH (0.545 mL, 0.54 mmole) in absolute EtOH (2 mL) was warmed in an oil bath set at 45° C. After 20 hr, the reaction was concentrated on the rotavap, and the residue was dissolved in H2O (1.5 mL). The solution was filtered to remove insoluble material, and the filtrate was carefully neutralized by dropwise addition of 1.0 N HCl (0.54 mL, 0.54 mmole). The precipitate was collected and dried in high vacuum to afford the title compound (68 mg, 58%) as a white solid: MS (ES) m/e 418.9 (M+H)+. Anal. Calcd for C25H26N2O4. 0.45 HCl: C, 69.05; H, 6.13; N. 6.44. Found: C, 69.25; H, 6.27; N. 6.16.

Workup

  1. temperaturewas warmed in an oil bath
  2. customset at 45° C
  3. concentrationthe reaction was concentrated on the rotavap
  4. dissolutionthe residue was dissolved in H2O (1.5 mL)
  5. filtrationThe solution was filtered
  6. customto remove insoluble material
  7. customThe precipitate was collected
  8. customdried in high vacuum

Sources & evidence

ORD record
ord-aa437940d91545da9a30acdef2778f63
Source dataset
uspto-grants-2003_06
Patent number
US06576643B2

Reaction notes

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