Benzene → HCID 22615398, compound

HRID 842797Notes

Reaction equation

HRID 842797 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][C:2]1=O.[CH2:8]([NH2:11])[CH2:9][NH2:10].C1(C)C=CC(S(O)(=O)=[O:19])=CC=1.[BH3-][C:24]#[N:25].[Na+].[CH:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>O>[NH2:10][CH2:9][CH2:8][NH:11][CH:4]1[CH2:5][CH2:6][N:1]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[C:24]([NH2:25])=[O:19])[CH2:2][CH2:3]1

Participants

7

Reactant 5

HCID 241BenzeneHCID 3301EthylenediamineHCID 6101p-Toluenesulfonic acidHCID 126652-PiperidoneHCID 5003444Sodium cyanoborohydride

Product 1

HCID 22615398HCID 22615398, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of the piperidone (2.5 g, 11.4543 mmol), ethylene diamine (6.89 g, 114.543 mmol) and p-toluene sulphonic acid (0.105 g, 0.57272 mmol) in benzene (100 mL) was refluxed under a Dean-Stark trap until cessation of water azeotrope. The solvent was removed in vacuo , diluted with MeOH (50 mL) and treated with NaBH3CN (0.714 g, 11.4543 mmol) at room temperature (1 h). The solvent was removed in vacuo, diluted with DCM (50 mL) and saturated aqueous sodium bicarbonate (25 mL), partitioned, extracted with DCM (2×50 mL), washed with saturated aqueous sodium bicarbonate (2×25 mL) and brine (50 mL), dried (Na2SO4), filtered and concentrated in vacuo and submitted to PCTLC (SiO2, 6 mm, 80/20/2 CHCl3—MeOH—NH4OH) affording the titled amine (67).

Workup

  1. customThe solvent was removed in vacuo
  2. additiondiluted with MeOH (50 mL)
  3. customThe solvent was removed in vacuo
  4. additiondiluted with DCM (50 mL) and saturated aqueous sodium bicarbonate (25 mL)
  5. custompartitioned
  6. extractionextracted with DCM (2×50 mL)
  7. washwashed with saturated aqueous sodium bicarbonate (2×25 mL) and brine (50 mL)
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dc19d3a08e05447d928df916f648ad64
Source dataset
uspto-grants-2002_04
Patent number
US06376503B1

Reaction notes

Loading…