Borane → HCID 12393827, compound

HRID 427110Notes

Reaction equation

HRID 427110 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:2]1.B.[O:20]1CCCC1>>[N:13]1([CH2:12][CH2:11][CH2:10][CH:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH2:1][CH:2]2[OH:20])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1

Participants

4

Reactant 3

HCID 6331BoraneHCID 8028Tetrahydrofuran2×HCID 12393826HCID 12393826, compound

Product 1

HCID 12393827HCID 12393827, compound

Procedure

1-[3-(3-Indenyl)propyl]piperidine (48.2 g, 0.2 M) is dissolved in 400 ml tetrahydrofuran and stirred in a nitrogen atmosphere while 400 ml 1 M borane in tetrahydrofuran is added dropwise over a period of 1 hour. The mixture is left stirring overnight at room temperature. Most of the solvent is then removed in vacuo. The viscous residue is dissolved in 500 ml 95% ethanol, treated with 20 g NaOH and then 65 ml of 30% H2O2 is added dropwise over a period of 30 minutes. The mixture is stirred at room temperature for 2 hours and then heated under reflux for 21/2 hours. The mixture is then taken to near dryness in vacuo. The residue is then extracted three times with benzene. The benzene extracts are dried, filtered and the solvent is removed in vacuo leaving 57 g of oil. The VPC of this material indicates ~97% of purity.

Workup

  1. additionis added dropwise over a period of 1 hour
  2. waitThe mixture is left
  3. customMost of the solvent is then removed in vacuo
  4. dissolutionThe viscous residue is dissolved in 500 ml 95% ethanol
  5. additiontreated with 20 g NaOH
  6. addition65 ml of 30% H2O2 is added dropwise over a period of 30 minutes
  7. stirringThe mixture is stirred at room temperature for 2 hours
  8. temperatureheated
  9. temperatureunder reflux for 21/2 hours
  10. extractionThe residue is then extracted three times with benzene
  11. dry with materialThe benzene extracts are dried
  12. filtrationfiltered
  13. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-a196e75909234733b1a531587b4af785
Source dataset
uspto-grants-1979_10
Patent number
US04172945

Reaction notes

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