Hydrochloric Acid → HCID 70230400, compound

HRID 249453Notes

Reaction equation

HRID 249453 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-tetrahydro-3-pyridine carboxylic acid methyl ester (4.33 g, 0.01147 mol) (prepared as described in Method D) was dissolved in ethanol (50 ml) and 10 N 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. 2 N 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-5a3b7372985f4c6aab2484901c3b41a7
Source dataset
uspto-grants-1993_05
Patent number
US05214057

Reaction notes

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