Hexane → HCID 22447278, compound

HRID 1154888Notes

Reaction equation

HRID 1154888 reaction equation
[S:1]1C=CC=[C:2]1[NH:6]C(O)=O.[OH-].[Na+].[CH3:12][C:13](Cl)([CH3:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH3:22][CH2:23][CH2:24][CH2:25][CH2:26]C>>[CH3:12][C:13]([CH3:20])([C:2]([N:6]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)=[S:1])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 4

HCID 8058HexaneHCID 14798Sodium HydroxideHCID 70281(1-Chloro-1-methylethyl)benzene2×HCID 19432670HCID 19432670, compound

Product 1

HCID 22447278HCID 22447278, compound

Procedure

To the so obtained aqueous thiolcarbamic acid salt solution was added 7.2 kg (179 moles) of 40% sodium hydroxide at 50° to 60° C., following which 27.6 kg (179 moles) of α,α-dimethylbenzyl chloride was added dropwise at the same temperature over the course of 20 minutes. After repeating this operation four times, a further addition dropwise of 69.0 kg (447 moles) of α,α-dimethylbenzyl chloride was made over the course of 30 minutes. The reaction mixture was then stirred at 50° to 60° C. for 1.5 hours to complete the reaction. The pH of the system ranged from 9.5 to 12.5 during the reaction. After cooling the reaction mixture, 80 liters of hexane was added, and the organic layer and the aqueous layer were separated. The organic layer was then washed with 80 liters of 2% hydrochloric acid and 80 liters of water. After distilling the hexane off from this hexane solution, a 0.5 liter ethanol solution of 0.5 kg of p-toluenesulfonic acid was added, and the mixture was reacted and distilled under reduced pressure (10 to 20 mm Hg) at below 110° C. The intended N-(α,α-dimethylbenzylthio-carbonyl)piperidine (93 kg) was obtained in the residue. On analysis by gas chromatography, this product was found to have a purity of 96.0%, and its yield based on thiolcarbamic acid salt was 78.5%. The melting point was 34.5°-36.0° C.

Workup

  1. additionwas added dropwise at the same temperature over the course of 20 minutes
  2. customwas made over the course of 30 minutes
  3. customthe reaction
  4. customThe pH of the system ranged from 9.5 to 12.5 during the reaction
  5. additionwas added
  6. customthe organic layer and the aqueous layer were separated
  7. washThe organic layer was then washed with 80 liters of 2% hydrochloric acid and 80 liters of water
  8. distillationAfter distilling the hexane off from this hexane solution
  9. additiona 0.5 liter ethanol solution of 0.5 kg of p-toluenesulfonic acid was added
  10. customthe mixture was reacted
  11. distillationdistilled under reduced pressure (10 to 20 mm Hg) at below 110° C

Sources & evidence

ORD record
ord-d4bde9cdc6724ac69d42be67d11c43c6
Source dataset
uspto-grants-1981_11
Patent number
US04298740

Reaction notes

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