Toluene → 1-(2,3-Dihydro-1H-inden-1-yl)piperidine

HRID 372806Notes

Reaction equation

HRID 372806 reaction equation
[C:1]1(=O)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[NH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[CH:1]1([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 67351-IndanoneHCID 8082Piperidine

Product 1

HCID 227581331-(2,3-Dihydro-1H-inden-1-yl)piperidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 100 g. of 1-indanone (0.758 mole) and 125 ml. of piperidine in 750 ml. of toluene is treated with 0.5 g. of p-toluenesulfonic acid and heated under reflux with a water take-off trap attached. Heating is continued for 48 hours. Solvent and excess piperidine are removed in vacuo and the residue is dissolved in 1500 ml. of absolute methanol. The resulting solution is stirred and treated portionwise with 50 g. of sodium borohydride below 30° C. After stirring several hours longer, the mixture is treated with a small amount of acetic acid then made strongly basic by the addition of sodium hydroxide solution. After 400 ml. of water is added, most of the methanol is removed in vacuo. Product is extracted into ether, dried over potassium hydroxide and distilled. 119.7 g. of 1-(1-indanyl)piperidine is collected at 101°-102° (0.2 mm.).

Workup

  1. additionA mixture of 100 g
  2. temperatureHeating
  3. customSolvent and excess piperidine are removed in vacuo
  4. dissolutionthe residue is dissolved in 1500 ml
  5. additiontreated portionwise with 50 g
  6. customof sodium borohydride below 30° C
  7. stirringAfter stirring several hours longer
  8. additionthe mixture is treated with a small amount of acetic acid
  9. additionthen made strongly basic by the addition of sodium hydroxide solution
  10. additionof water is added, most of the methanol
  11. customis removed in vacuo
  12. extractionProduct is extracted into ether
  13. dry with materialdried over potassium hydroxide
  14. distillationdistilled
  15. customof 1-(1-indanyl)piperidine is collected at 101°-102° (0.2 mm.)

Sources & evidence

ORD record
ord-16745860f7f64203bfce44873950d06c
Source dataset
uspto-grants-1978_05
Patent number
US04092318

Reaction notes

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