Sulfuric Acid → HCID 13281039, compound

HRID 648652Notes

Reaction equation

HRID 648652 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8](O)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:5]=[CH:6][CH:7]=1.[C:22]([CH2:24][C:25]1[CH:35]=[CH:34][C:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:27][CH:26]=1)#[N:23].S(=O)(=O)(O)[OH:37]>ClC1C=CC=CC=1Cl>[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]([NH:23][C:22]([CH2:24][C:25]2[CH:35]=[CH:34][C:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:27][CH:26]=2)=[O:37])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 11989373ethyl 4-(cyanomethyl)benzoateHCID 54128206HCID 54128206, compound

Product 1

HCID 13281039HCID 13281039, compound

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent2×

Procedure

A mixture of 0.22 gm (0.8 m mol) of α-(3-methyl-phenyl)-2-piperidino-benzyl alcohol and 0.15 gm (0.8 m mol) of ethyl 4-cyanomethyl-benzoate in 2 ml of o-dichlorobenzene was added dropwise, at ambient temperature, to 1.5 ml of o-dichlorobenzene and 1.5 ml of concentrated sulfuric acid. After stirring for two hours, the mixture was poured onto ice water, extracted once with ether, made alkaline with dilute sodium hydroxide solution, and extracted with chloroform. The chloroform extract was concentrated by evaporation, and the residue was recrystallized from ethanol.

Workup

  1. additionthe mixture was poured onto ice water
  2. extractionextracted once with ether
  3. extractionextracted with chloroform
  4. extractionThe chloroform extract
  5. concentrationwas concentrated by evaporation
  6. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-c2372fe392ae404f83039c363e8b0916
Source dataset
uspto-grants-1988_04
Patent number
US04735959

Reaction notes

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