Water → HCID 19094715, compound

HRID 487343Notes

Reaction equation

HRID 487343 reaction equation
[CH3:1][O:2][CH:3]([O:14][CH3:15])[C:4]1[CH:9]=[C:8](Cl)[CH:7]=[CH:6][C:5]=1[N+:11]([O-:13])=[O:12].[OH:16][CH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.O>CN(C)C=O>[CH3:1][O:2][CH:3]([O:14][CH3:15])[C:4]1[CH:9]=[C:8]([N:20]2[CH2:21][CH2:22][CH:17]([OH:16])[CH2:18][CH2:19]2)[CH:7]=[CH:6][C:5]=1[N+:11]([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 962WaterHCID 79341Piperidin-4-olHCID 35700934-Chloro-2-(dimethoxymethyl)-1-nitrobenzene

Product 1

HCID 19094715HCID 19094715, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5 g of 5-chloro-2-nitrobenzaldehyde dimethylacetal and 8.8 g of 4-hydroxypiperidine in 20 ml of N,N-dimethylformamide was heated at 80 ° C. for 14 hr. The reaction mixture was poured into water, and extracted with ethyl acetate. The extract was washed with water, dried, and evaporated under a reduced pressure. The residue was purified by a silica gel column chromatography to give 4.3 g of 5-(4-hydroxypiperidino)-2-nitrobenzaldehyde dimethylacetal.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. customdried
  4. customevaporated under a reduced pressure
  5. customThe residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-486ac7ce92b04adab616dae8f9bc4aa1
Source dataset
uspto-grants-1994_03
Patent number
US05294718

Reaction notes

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