Hydrochloric Acid → {4-[Dimethylamino-(3-fluorophenyl)-methyl]-cyclohexyl}-acetaldehyde

HRID 557520Notes

Reaction equation

HRID 557520 reaction equation
[CH3:1][N:2]([CH:4]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=1)[CH:5]1[CH2:10][CH2:9][CH:8]([CH:11]=O)[CH2:7][CH2:6]1)[CH3:3].C1C[O:23][CH2:22]C1.Cl>O>[CH3:1][N:2]([CH:4]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=1)[CH:5]1[CH2:10][CH2:9][CH:8]([CH2:11][CH:22]=[O:23])[CH2:7][CH2:6]1)[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 866278884-[Dimethylamino-(3-fluorophenyl)-methyl]-cyclohexane-carbaldehyde

Product 1

HCID 86627887{4-[Dimethylamino-(3-fluorophenyl)-methyl]-cyclohexyl}-acetaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The aldehyde 34 (13.69 g, 52 mmol) dissolved in abs. THF (90 ml) was then added dropwise at RT, and stirring was carried out overnight at RT. Hydrolysis was carried out dropwise with water (50 ml) and 6N HCl (150 ml), while cooling with ice-water. After 1 hour's stirring at RT, extraction with ether was carried out ten times (50 ml each time). The aqueous phase was adjusted to pH 11 with 5N NaOH, extracted by shaking three times with ethyl acetate (100 ml each time), dried over Na2SO4 and concentrated in vacuo. The crude product was purified by flash chromatography with ethyl acetate/cyclohexane (1:1).

Workup

  1. customHydrolysis
  2. stirringAfter 1 hour's stirring at RT
  3. extractionextraction with ether
  4. extractionextracted
  5. stirringby shaking three times with ethyl acetate (100 ml each time)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by flash chromatography with ethyl acetate/cyclohexane (1:1)

Sources & evidence

ORD record
ord-7a2499c3d2a34f7284388c6621ac85aa
Source dataset
uspto-grants-2011_11
Patent number
US08058475B2

Reaction notes

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