3-Hydroxybenzaldehyde → HCID 21846078, compound

HRID 619195Notes

Reaction equation

HRID 619195 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].C([O-])([O-])=O.[K+].[K+].Cl.[CH3:17][N:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]1[CH2:24]Cl>CC#N>[CH3:17][N:18]1[CH2:24][CH2:19][CH2:20][CH2:21][CH:22]([O:1][C:2]2[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=2)[CH:5]=[O:6])[CH2:23]1

Participants

5

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 126443922-(Chloromethyl)-1-methylpiperidine--hydrogen chloride (1/1)

Product 1

HCID 21846078HCID 21846078, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-hydroxybenzaldehyde (3.66 g, 0.03 mol), K2CO3 (12.43 g, 0.09 mol), and CH3CN (100 ml) was stirred at room temperature for 1/2 hour, then N-methyl-2-chloromethylpiperidine hydrochloride (5.49 g, 0.03 mol) was added. The reaction mixture was stirred until the reaction was complete, then the solvent was removed in vacuo and the residue was partitioned between CHCl3 and water. The aqueous layer was extracted with CHCl3 (3×100 ml) and the combined organic layers were concentrated in vacuo to afford 3-(1-methyl-3-hexahydroazepinyloxy)benzaldehyde.

Workup

  1. stirringThe reaction mixture was stirred until the reaction
  2. customthe solvent was removed in vacuo
  3. customthe residue was partitioned between CHCl3 and water
  4. extractionThe aqueous layer was extracted with CHCl3 (3×100 ml)
  5. concentrationthe combined organic layers were concentrated in vacuo

Sources & evidence

ORD record
ord-01ad383acdb1463d8d18e12d41747ecc
Source dataset
uspto-grants-1999_09
Patent number
US05958929

Reaction notes

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