4-Chlorobenzaldehyde → HCID 9846708, compound

HRID 1740879Notes

Reaction equation

HRID 1740879 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.[Cl:29][C:30]1[CH:37]=[CH:36][C:33]([CH:34]=O)=[CH:32][CH:31]=1>C(COC)OC.C(OC(=O)C)C>[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]([Cl: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

6

Reactant 3

HCID 77264-ChlorobenzaldehydeHCID 1237760HCID 1237760, compoundHCID 178418339Butyllithium

Product 1

HCID 9846708HCID 9846708, compoundYield 65.7%

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 19.16 g (58.1 mmol) of N-(1-benzylpiperidin-4-yl)-benzene sulfonamide in 300 mL of dimethoxyethane at 0° C. was added 46.4 mL (116.1 mmol) of a n-butyllithium (2.5 M) slowly via addition funnel. The mixture was stirred using an overhead stirrer for 45 minutes at 0° C., then 9.61 g (63.9 mmol) of p-chlorobenzaldehyde was added in one portion. The mixture was allowed to warm to room temperature, diluted with 1 liter of ethylacetate and washed 2×500 mL of water followed by 500 mL of brine. The organic phase was separated, dried (MgSO4), and concentrated in vacuo. The residue was flash chromatographed over 300 g of silica gel (eluted with ethylacetate:heptane-2:1) to afford 17.3 g of product as an orange paste.

Workup

  1. additionslowly via addition funnel
  2. customfor 45 minutes
  3. customat 0° C.
  4. washwashed 2×500 mL of water
  5. customThe organic phase was separated
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customchromatographed over 300 g of silica gel (eluted with ethylacetate:heptane-2:1)

Sources & evidence

ORD record
ord-f0fb4560e01f4b4282e34e780d74dcb3
Source dataset
uspto-grants-1999_10
Patent number
US05972963

Reaction notes

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