HCID 68581004, compound → Citalopram aldehyde

HRID 2235832Notes

Reaction equation

HRID 2235832 reaction equation
[O:1]1CCO[CH:2]1[CH2:6][CH2:7][C:8]1([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[C:16]2[C:11](=[CH:12][C:13]([C:17]#[N:18])=[CH:14][CH:15]=2)[CH2:10][O:9]1>CC(C)=O.Cl>[F:25][C:22]1[CH:21]=[CH:20][C:19]([C:8]2([CH2:7][CH2:6][CH:2]=[O:1])[C:16]3[C:11](=[CH:12][C:13]([C:17]#[N:18])=[CH:14][CH:15]=3)[CH2:10][O:9]2)=[CH:24][CH:23]=1

Participants

4

Reactant 1

HCID 68581004HCID 68581004, compound

Product 1

HCID 9944000Citalopram aldehydeYield 107.3%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 313Hydrochloric AcidSolvent2×

Procedure

1-(2-[1, 3]-dioxolan-2-yl-ethyl)-1-(4-fluorophenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile (6 g) was dissolved in a mixture of acetone (100 mL) and aqueous HCl (5N, 30 mL). The reaction mixture was stirred at room temperature for 60 h, and concentrated to remove acetone. The aqueous solution was extracted with ethyl acetate (40 mL), and concentrated to give a crude oil. It was dissolved in acetone (80 mL) and aqueous HCl (5N, 25 mL), stirred for 3 h, and concentrated to remove acetone. The aqueous solution was extracted with ethyl acetate (40 mL), washed with water, and concentrated to give the pure product 7 (5.6 g). 1H NMR (CDCl3, δ): 2.22-2.64 (M, 4H), 5.14 (s, 2H), 6.94-7.06 (m, 2H), 7.40-7.63 (m, 5H), 9.70 (s, 1H).

Workup

  1. concentrationconcentrated
  2. customto remove acetone
  3. extractionThe aqueous solution was extracted with ethyl acetate (40 mL)
  4. concentrationconcentrated
  5. customto give a crude oil
  6. concentrationconcentrated
  7. customto remove acetone
  8. extractionThe aqueous solution was extracted with ethyl acetate (40 mL)
  9. washwashed with water
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-5779ff55d68e4a85b6d5e9cbdd130579
Source dataset
uspto-grants-2010_05
Patent number
US07714023B2

Reaction notes

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