HCID 21834627, compound → N-Methyl-3,3-diphenylpropylamine

HRID 1292669Notes

Reaction equation

HRID 1292669 reaction equation
[CH2:1]([N:8]([CH2:10][CH2:11][CH:12]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)C)C1C=CC=CC=1>CO.Cl.[OH-].[Pd+2].[OH-]>[CH3:1][NH:8][CH2:10][CH2:11][CH:12]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 1

HCID 21834627HCID 21834627, compound

Product 1

HCID 119812N-Methyl-3,3-diphenylpropylamine

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A solution of N-benzyl-N-methyl-3,3-diphenylpropylamine (1.03 g, 3.27 mmol) in methanol (35 ml) and aq. HCl (0.27 ml, of a 12.1M aq. solution, 3.3 mmol) was purged with argon and palladium hydroxide (405 mg) added. The flask was evacuated and shaken under an atmosphere of hydrogen (50 psi) for 18 hrs. The hydrogen was replaced by argon and the catalyst removed by filtration. The filtrate was treated with aq. NaOH (100 ml of a 1M solution) and extracted into Et2O. The organic extracts were dried (Na2SO4) and evaporated in vacuo to afford the title compound as an oil.

Workup

  1. additionadded
  2. customThe flask was evacuated
  3. customthe catalyst removed by filtration
  4. additionThe filtrate was treated with aq. NaOH (100 ml of a 1M solution) and
  5. extractionextracted into Et2O
  6. dry with materialThe organic extracts were dried (Na2SO4)
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-048d966495944deab7ac9ceb39c40f5b
Source dataset
uspto-grants-1998_05
Patent number
US05756528

Reaction notes

Loading…