Sulfuric Acid → 4-[N-(4-Chloro-benzyl)-amino]-cyclohexanone

HRID 476962

Reaction equation

[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][NH:7][CH:8]2[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[K+].[K+].[OH-].[Na+]>>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][NH:7][CH:8]2[CH2:9][CH2:10][C:11](=[O:14])[CH2:12][CH2:13]2)=[CH:4][CH:3]=1

Participants

Reactant 4

HCID 1118Sulfuric Acid

HCID 14798Sodium Hydroxide

HCID 24502Potassium Dichromate

HCID 136706584-(4-Chloro-benzylamino)-cyclohexanol

Product 1

HCID 136706644-[N-(4-Chloro-benzyl)-amino]-cyclohexanone

Conditions

Temperature: 50 °C

Procedure

23.9 g (0.1 Mol) of 4-[N-(4-chlorobenzyl)-amino]-cyclohexanol are suspended in 125 ml of ice water and 32 ml of concentrated sulphuric acid are added. Then 29.4 g (0.1 Mol) of potassium dichromate are added in 2 batches and the mixture is heated for 5 hours at 50° C. It is then cooled, made alkaline with sodium hydroxide solution and extracted with chloroform. After concentration, a yellowish oily liquid is obtained.

Workup

temperatureIt is then cooled
extractionextracted with chloroform
concentrationAfter concentration
customa yellowish oily liquid is obtained

Sources & evidence

ORD record: ord-874c5a08b0844fab87f211f243ad1ec2
Source dataset: uspto-grants-1989_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04886812

Linked notes

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