Hydrochloric Acid → HCID 45261661, compound

HRID 1460650Notes

Reaction equation

HRID 1460650 reaction equation
C([O:3][C:4]([C@@H:6]1[CH2:11][CH2:10][CH2:9][N:8]([CH2:12][CH2:13][O:14]/[CH:15]=[C:16](/[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH3:29])\[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:7]1)=[O:5])C.[OH-].[Na+].Cl.[Cl:33]CCl>C(O)C.CC(C)=O>[ClH:33].[CH3:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1/[C:16](/[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[CH:15]/[O:14][CH2:13][CH2:12][N:8]1[CH2:9][CH2:10][CH2:11][C@@H:6]([C:4]([OH:5])=[O:3])[CH2:7]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 10502731HCID 10502731, compound

Product 1

HCID 45261661HCID 45261661, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 702EthanolSolvent

Procedure

E-(R)-1-[2-[[2-(2-Methylphenyl)-2-phenylethenyl]oxy]ethyl]-3-piperidine carboxylic acid ethyl ester (1.1 g, 0.0028 mol) (prepared as described in Method A) was dissolved in ethanol (5 ml) and 12N sodium hydroxide solution (0.7 ml) was introduced. After stirring the solution at room temperature for 2 h, 37% hydrochloric acid solution (ca. 1.0 ml) was added (with cooling) followed by dichloromethane (300 ml) and the mixture was dried (Na2SO4). Filtration and evaporation of the filtrate gave a residue, which was co-evaporated with acetone. The solid product was triturated with ethyl acetate, collected by filtration and dried in vacuo to provide the title compound (0.70 g, 62%), m.p. 195-196.

Workup

  1. temperature(with cooling)
  2. dry with materialthe mixture was dried (Na2SO4)
  3. filtrationFiltration and evaporation of the filtrate
  4. customgave a residue, which
  5. customThe solid product was triturated with ethyl acetate
  6. filtrationcollected by filtration
  7. customdried in vacuo

Sources & evidence

ORD record
ord-d31f91ba656b4b26a449a709c8e615ff
Source dataset
uspto-grants-1991_12
Patent number
US05071859

Reaction notes

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