Sodium Hydroxide → 4-(Dibenz[b,e]oxepin-11(6H)-ylidene)-1-piperidinepropionic acid

HRID 2371713Notes

Reaction equation

HRID 2371713 reaction equation
[CH:1]1[C:11]2[C:10](=[C:12]3[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][C:20]([O:22]CC)=[O:21])[CH2:14][CH2:13]3)[C:9]3[CH:25]=[CH:26][CH:27]=[CH:28][C:8]=3[CH2:7][O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>CO>[CH:1]1[C:11]2[C:10](=[C:12]3[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][C:20]([OH:22])=[O:21])[CH2:14][CH2:13]3)[C:9]3[CH:25]=[CH:26][CH:27]=[CH:28][C:8]=3[CH2:7][O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10276748Ethyl 4-(dibenz[b,e]oxepin-11(6H)-ylidene)-1-piperidinepropionate

Product 1

HCID 99283214-(Dibenz[b,e]oxepin-11(6H)-ylidene)-1-piperidinepropionic acidYield 96.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3.70 g of ethyl 4-(dibenz[b,e]oxepin-11(6H)-ylidene)-1-piperidinepropionate, 9.9 ml of 2N sodium hydroxide aqueous solution and 40 ml of methanol was refluxed for 30 min and concentrated. Water was added to the residue, adjusted to pH 3 with 10% hydrochloric acid. The precipitate was collected by filtration and washed with water and ether to give 3.30 g of pale yellow crystals, which were recrystallized from a mixture of water and N,N-dimethylformamide to give 2.75 g of pale yellow crystals, mp 142°-143° C.

Workup

  1. temperaturewas refluxed for 30 min
  2. concentrationconcentrated
  3. additionWater was added to the residue
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with water and ether

Sources & evidence

ORD record
ord-60b897846e4441a5ba495d85d25adcf5
Source dataset
uspto-grants-1992_03
Patent number
US05095022

Reaction notes

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