Hydrochloric Acid → HCID 70230400, compound

HRID 1460670Notes

Reaction equation

HRID 1460670 reaction equation
[ClH:1].F[C:3]1[CH:4]=[C:5]([C:9]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25](F)[CH:24]=2)=[CH:10][O:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][CH:17]=[C:16]([C:20]([OH:22])=[O:21])[CH2:15]2)[CH:6]=[CH:7][CH:8]=1.[OH-].[Na+].O.Cl>C(O)C>[ClH:1].[C:23]1([C:9]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:3][CH:4]=2)=[CH:10][O:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][CH:17]=[C:16]([C:20]([OH:22])=[O:21])[CH2:15]2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 45264923HCID 45264923, compound

Product 1

HCID 70230400HCID 70230400, compoundYield 95.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-[2-[[2,2-Diphenylethenyl]oxy]ethyl]-1,2,5,6-tetrahydro3-pyridine carboxylic acid methyl ester (4.33 g, 0.01147 mol) (prepared as described in Method D) was dissolved in ethanol (50 ml) and 10N sodium hydroxide solution (11.5 ml) was introduced, followed by water (5 ml). The solution was stirred at room temperature for 2.5 h and stored at 4° C. for 18 h. 2N hydrochloric acid solution was added until the pH reached ca. 2, and the mixture was extracted with dichloromethane (3×60 ml). The combined extracts were dried (MgSO4) and evaporated to give a foam (4.24 g) which was crystallized from 2-propanol to provide the title compound (2.32 g, 52%) as a white solid, m.p. 173°-176°.

Workup

  1. waitstored at 4° C. for 18 h
  2. extractionthe mixture was extracted with dichloromethane (3×60 ml)
  3. dry with materialThe combined extracts were dried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-cf1efd31c1e54f9d86ea50bfa27c99c2
Source dataset
uspto-grants-1991_12
Patent number
US05071859

Reaction notes

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