Sodium Hydroxide → HCID 12071479, compound

HRID 1369242Notes

Reaction equation

HRID 1369242 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][C@H: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][C@H: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 12071478HCID 12071478, compound

Product 1

HCID 12071479HCID 12071479, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl (R)-10,11-dihydro-3-[3-(pyridin-2-ylamino)-1-propyloxy]-5H-dibenzo[a,d]cycloheptene-10-acetate (0.4 g, 0.93 mmole) and 1.0 N NaOH (1.1 mL, 1.1 mmole) in absolute EtOH (10 mL) was warmed in an oil bath set at 50° C. After 18 hr, the reaction was concentrated on the rotavap and the residue was dissolved in H2O. The aqueous solution was adjusted to pH 4 with 3 N HCl, and the solid precipitate was collected and washed with H2O. The material was dried in high vacuum at 40° C. to afford the title compound (0.36 g, 96%) as a nearly colorless solid: [α]D +50.8° (c=0.12, CH3OH); MS (ES) m/e 403 (M+H)+. Anal. Calcd for C25H26N2O3.0.5 H2O: C, 72.97; H, 6.61; 6.80. Found: C, 73.09; H, 6.38; N, 6.58.

Workup

  1. temperaturewas warmed in an oil bath
  2. customset at 50° C
  3. concentrationthe reaction was concentrated on the rotavap
  4. dissolutionthe residue was dissolved in H2O
  5. customthe solid precipitate was collected
  6. washwashed with H2O
  7. customThe material was dried in high vacuum at 40° C.

Sources & evidence

ORD record
ord-c4357b7030534e9ab7f8a377bd546d68
Source dataset
uspto-grants-2003_06
Patent number
US06576643B2

Reaction notes

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