Sodium Hydroxide → 2-(1,2,3,4,10,14b-Hexahydrodibenzo[c,f]pyrazino[1,2-a]azepin-2-yl)acetic acid

HRID 2225374Notes

Reaction equation

HRID 2225374 reaction equation
[OH-].[Na+].[CH2:3]1[CH:8]2[C:9]3[CH:21]=[CH:20][CH:19]=[CH:18][C:10]=3[CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:7]2[CH2:6][CH2:5][N:4]1[CH2:22][C:23]([O:25]CC)=[O:24]>CO>[CH2:3]1[CH:8]2[C:9]3[CH:21]=[CH:20][CH:19]=[CH:18][C:10]=3[CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:7]2[CH2:6][CH2:5][N:4]1[CH2:22][C:23]([OH:25])=[O:24]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19004075Ethyl (1,2,3,4,10,14b-hexahydrodibenzo[c,f]pyrazino[1,2-a]azepin-2-yl)acetate

Product 1

HCID 104479932-(1,2,3,4,10,14b-Hexahydrodibenzo[c,f]pyrazino[1,2-a]azepin-2-yl)acetic acidYield 86.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2N Aqueous sodium hydroxide solution (5 ml) was added to a solution of 1.68 g of ethyl 2-(1,2,3,4,10,14b-hexahydrodibenzo[c,f]pyrazino[1,2-a]azepin-2-yl)acetate in 17 ml of methanol. The solution was refluxed for 30 min and then concentrated. The residue was dissolved in hot water and the solution was neutralized with 0.5N hydrochloric acid. The precipitates were collected by filtration to give 1.33 g of colorless crystals, which were recrystallized from aqueous ethanol to give colorless needles, mp 162°-163° C.

Workup

  1. temperatureThe solution was refluxed for 30 min
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in hot water
  4. filtrationThe precipitates were collected by filtration

Sources & evidence

ORD record
ord-e296ad53eab84d27bf21020e7a91bcd4
Source dataset
uspto-grants-1994_09
Patent number
US05344828

Reaction notes

Loading…