Sodium Hydroxide → HCID 11742647, compound

HRID 1369252Notes

Reaction equation

HRID 1369252 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][C@@H:21]([CH2:23][C:24]([O:26]CC)=[O:25])[C:20]4[CH:29]=[CH:30][CH:31]=[CH:32][C:19]=4[CH2:18][C:17]=3[CH:33]=2)[CH:3]=1.[OH-].[Na+]>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][C@@H:21]([CH2:23][C:24]([OH:26])=[O:25])[C:20]4[CH:29]=[CH:30][CH:31]=[CH:32][C:19]=4[CH2:18][C:17]=3[CH:33]=2)[CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54315823HCID 54315823, compound

Product 1

HCID 11742647HCID 11742647, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl (S)-10,11-dihydro-3-[3-(4-methylpyridin-2-ylamino)-1-propyloxy]-5H-dibenzo[a,d]cycloheptene-10-acetate (2.08 g, 4.69 mmole) and 1.0 N NaOH (7.0 ml, 7.0 mmole) in absolute EtOH (45 mL) was warmed in an oil bath set at 45° C. After 18 hr, the reaction was concentrated on the rotavap and the pH was adjusted to 7 with 1.0 N HCl. The solid precipitate was collected and washed with H2O. Drying overnight afforded the title compound (1.61 g, 82%) as a nearly colorless solid: MS (ES) m/e 417.4 (M+H)+. Anal. Calcd for C26H28N2O3.1.0 H2O: C, 71.87; H, 6.96; N, 6.45. Found: C, 71.63; H, 6.96; N, 6.30.

Workup

  1. temperaturewas warmed in an oil bath
  2. customset at 45° C
  3. concentrationthe reaction was concentrated on the rotavap
  4. customThe solid precipitate was collected
  5. washwashed with H2O
  6. customDrying overnight

Sources & evidence

ORD record
ord-6e7599a6b0bd4ae88ecd7f51767bdc4b
Source dataset
uspto-grants-2003_06
Patent number
US06576643B2

Reaction notes

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