Diethyl Ether → HCID 9910901, compound

HRID 1740880Notes

Reaction equation

HRID 1740880 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:17])=[O:16])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[F:29][C:30]1[CH:37]=[CH:36][C:33]([CH:34]=O)=[CH:32][CH:31]=1.CCOCC>C(COC)OC.CO>[CH2:1]([N:8]1[CH2:9][CH2:10][CH:11]([N:14]2[CH:34]([C:33]3[CH:36]=[CH:37][C:30]([F:29])=[CH:31][CH:32]=3)[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[S:15]2(=[O:17])=[O:16])[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 680234-FluorobenzaldehydeHCID 1237760HCID 1237760, compoundHCID 178418339Butyllithium

Product 1

HCID 9910901HCID 9910901, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 80711,2-DimethoxyethaneSolvent2×

Procedure

A solution of N-(l-benzylpiperidin-4-yl)benzenesulfonamide from Example 1 above, (18.7 g, 56.5 mmol) and 210 ml dimethoxyethane was chilled at 0° C. under N2, followed by a slow addition over 25 minutes of 2.3 equivalent of n-butyl lithium (52 ml, 2.5 N/hexanes, 130 mmol) keeping the temperature below 15° C. After mechanically stirring for 35 minutes longer, 4-fluorobenzaldehyde (7.4 g, 59 mmol) in 50 ml dimethoxyethane was added at 5° C., and the reaction was stirred for 2 hours. Ether (400 ml) was added, and the reaction was washed with water and brine, dried (MgSO4), and concentrated in vacuo. The residue was chromatographed on silica gel eluting with CHCl3 to CHCl3 :5% MeOH to afford 11.85 g (46% yield) of the intermediate as a foam.

Workup

  1. customthe temperature below 15° C
  2. stirringthe reaction was stirred for 2 hours
  3. washthe reaction was washed with water and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on silica gel eluting with CHCl3 to CHCl3

Sources & evidence

ORD record
ord-11df61dcfa1441e0aa789456c557c498
Source dataset
uspto-grants-1999_10
Patent number
US05972963

Reaction notes

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