Benzaldehyde → HCID 18678541, compound

HRID 1634738Notes

Reaction equation

HRID 1634738 reaction equation
C(=O)C1C=CC=CC=1.[NH2:9][CH2:10][CH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.[N+:17]([C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1)([O-:19])=[O:18].C([N:33](C(C)C)CC)(C)C.OS([O-])(=O)=O.[K+]>C1(C)C=CC=CC=1.O>[NH2:9][CH2:10][CH:11]1[CH2:16][CH2:15][N:14]([C:24]2[CH:25]=[C:20]([N+:17]([O-:19])=[O:18])[CH:21]=[CH:22][C:23]=2[S:26]([NH2:33])(=[O:28])=[O:27])[CH2:13][CH2:12]1

Participants

8

Reactant 5

HCID 240BenzaldehydeHCID 74044-Nitrobenzenesulfonyl chlorideHCID 235274-(Aminomethyl)piperidineHCID 81531DiisopropylethylamineHCID 516920Potassium bisulfate

Product 1

HCID 18678541HCID 18678541, compoundYield 103.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A solution of benzaldehyde (20.3 mL, 200 mmol) and 4-aminomethylpiperidine (22.8 g, 200 mmol) in 250 mL toluene was heated at reflux until 3.6 mL of H2O was collected in a Dean-Stark trap. To the cooled reaction mixture was added 4-nitrobenzenesulfonyl chloride (44.3 g, 200 mmol) and diisopropylethyl amine (34.8 mL, 200 mmol) and stirring was continued for 1 hour. The intermediate imine was decomposed by the addition of 200 mL of 1N KHSO4 solution. The solids formed were filtered, washed sequentially with water and ether. The collected solids were dried to provide 65 g of the title compound.

Workup

  1. customwas collected in a Dean-Stark trap
  2. customTo the cooled reaction mixture
  3. customThe solids formed
  4. filtrationwere filtered
  5. washwashed sequentially with water and ether
  6. customThe collected solids were dried

Sources & evidence

ORD record
ord-c0da7da03ee4423baee175eb024f480c
Source dataset
uspto-grants-2003_01
Patent number
US06506901B2

Reaction notes

Loading…