Sulfuric Acid → HCID 12941761, compound

HRID 1155797Notes

Reaction equation

HRID 1155797 reaction equation
[CH3:1][C:2]1([CH3:17])[CH2:13][CH:12]=[CH:11][CH2:10][CH2:9][CH:8]=[CH:7][CH2:6][CH:5]([CH:14]([CH3:16])[CH3:15])[N:4]=[CH:3]1.S(=O)(=O)(O)[OH:19].[H][H]>O.[Pt]>[CH3:1][C:2]([CH3:17])([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH:5]([CH:14]([CH3:16])[CH3:15])[NH2:4])[CH2:3][OH:19]

Participants

6

Reactant 3

HCID 1118Sulfuric Acid2×HCID 5575123,3-Dimethyl-12-isopropyl-1-aza-1,5,9-cyclododecatrieneHCID 178418361HCID 178418361, compound

Product 1

HCID 12941761HCID 12941761, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 962WaterSolvent

Procedure

218 g (0.935 mol) of 3,3-dimethyl-12-isopropyl-1-aza-1,5,9-cyclododecatriene are added dropwise in the course of 15 minutes to a solution of 150 g (1.53 mols) of sulphuric acid in one liter of water. Aldehyde impurities are removed by a subsequent 20 minute steam distillation. The aqueous sulphuric acid solution is then hydrogenated at normal pressure and 20°-25° C. in the presence of a platinum-on-charcoal catalyst (5% by weight of platinum), with the absorption of 3 mols of hydrogen, to give 2,2-dimethyl-11-isopropyl-11-aminoundecanol. After filtering off the catalyst, the aqueous solution is neutralised with concentrated sodium hydroxide solution and the oily amino-alcohol which separates out is extracted by shaking with toluene and distilled. 196 g (0.763 mol) of 2,2-dimethyl-11-isopropyl-11-aminoundecanol are obtained, corresponding to a yield of 81.5% of theory; boiling point 110° C./0.02 mm Hg; nD20 =1.4684.

Workup

  1. customAldehyde impurities are removed by a subsequent 20 minute
  2. distillationsteam distillation

Sources & evidence

ORD record
ord-53d8b36b86e7400dba72b24685aa9c3a
Source dataset
uspto-grants-1982_06
Patent number
US04332969

Reaction notes

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