Hydrochloric Acid → 1-[2-Bis(4-fluorophenyl)methoxyethyl]-4-piperidinecarbaldehyde

HRID 487136Notes

Reaction equation

HRID 487136 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[O:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][C:15](=[CH:18][O:19]C)[CH2:14][CH2:13]2)=[CH:4][CH:3]=1.Cl.O1CCCC1.[OH-].[Na+]>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[O:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][CH:15]([CH:18]=[O:19])[CH2:14][CH2:13]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 99994121-[2-Bis(4-fluorophenyl)methoxyethyl]-4-methoxymethylidenepiperidine

Product 1

HCID 99757211-[2-Bis(4-fluorophenyl)methoxyethyl]-4-piperidinecarbaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

420 mg of 1-[2-bis(4-fluorophenyl)methoxyethyl]-4-methoxymethylidenepiperidine (prepared as described in Preparation 5) were added to a mixture of 1.5 ml of 10% w/v aqueous hydrochloric acid and 3 ml of tetrahydrofuran, and the resulting mixture Was then stirred for 2 hours at room temperature. At the end of this time, water was added to the reaction mixture, and it was neutralized by the addition of a 5% w/v aqueous solution of sodium hydroxide and extracted with ethyl acetate. The extract was purified by silica gel column chromatography. Elution with 3% by volume methanol in methylene chloride afforded 434 mg (a quantitative yield) of the title compound as an oil, whose properties were the same as those of the product of step (a).

Workup

  1. extractionextracted with ethyl acetate
  2. customThe extract was purified by silica gel column chromatography
  3. washElution with 3% by volume methanol in methylene chloride

Sources & evidence

ORD record
ord-e36cb6e6327e45bfbf2c5caef61de6fd
Source dataset
uspto-grants-1994_03
Patent number
US05294623

Reaction notes

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