N,N-Diethylethylenediamine → N,N-Diethyl-N'-(4'-trifluoromethylbiphenyl-4-ylmethyl)-ethane-1,2-diamine

HRID 1767143Notes

Reaction equation

HRID 1767143 reaction equation
[CH2:1]([N:3]([CH2:7][CH3:8])[CH2:4][CH2:5][NH2:6])[CH3:2].[F:9][C:10]([F:26])([F:25])[C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=2)=[CH:13][CH:12]=1>C1(C)C=CC=CC=1.[Pd]>[CH2:1]([N:3]([CH2:7][CH3:8])[CH2:4][CH2:5][NH:6][CH2:21][C:20]1[CH:19]=[CH:18][C:17]([C:14]2[CH:15]=[CH:16][C:11]([C:10]([F:9])([F:25])[F:26])=[CH:12][CH:13]=2)=[CH:24][CH:23]=1)[CH3:2]

Participants

5

Reactant 2

HCID 60993N,N-DiethylethylenediamineHCID 27827124'-(Trifluoromethyl)-4-biphenylcarbaldehyde

Product 1

HCID 11233414N,N-Diethyl-N'-(4'-trifluoromethylbiphenyl-4-ylmethyl)-ethane-1,2-diamineYield 100.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

N,N-diethylethylene diamine (2.50 kg, 21.12 moles) was added to a solution of 4-(4-trifluoromethylphenyl)benzaldehyde (3.54 kg, 14.08 moles) in toluene (21 L) and rinsed in with toluene (14 L) with stirring. The resultant solution was stirred at 17-21° C. for ca. 96 hours. The solution was then transferred to a hydrogenation vessel containing 5% palladium on alumina (0.213 kg, 0.11 moles Pd) and rinsed in with toluene (37 L). The mixture was hydrogenated at 19−27° C., 50 psig hydrogen for 1 hour until no further hydrogen was consumed. The catalyst was removed by filtration through celite (0.5 kg) and the celite bed was washed with toluene (14 L). The combined filtrate and wash were washed with process water (3×14 L) then the toluene removed by distillation at 20-80° C. in vacuo to give the title compound as a pale yellow oil (4.96 kg, 97.3%). 1H NMR (CDCl3) δ 1.01 (6H, t), 2.52 (4H, q), 2.58 (2H, t), 2.70 (2H, t),3.86 (2H, s), 7.42 (2H, d), 7.43 (2H, d), 7.68 (4H, s).

Workup

  1. washrinsed in with toluene (14 L)
  2. stirringThe resultant solution was stirred at 17-21° C. for ca. 96 hours
  3. customThe solution was then transferred to a hydrogenation vessel
  4. washrinsed in with toluene (37 L)
  5. customwas hydrogenated at 19−27° C.
  6. custom50 psig hydrogen for 1 hour until no further hydrogen was consumed
  7. customThe catalyst was removed by filtration through celite (0.5 kg)
  8. washthe celite bed was washed with toluene (14 L)
  9. washThe combined filtrate and wash
  10. washwere washed with process water (3×14 L)
  11. customthe toluene removed by distillation at 20-80° C. in vacuo

Sources & evidence

ORD record
ord-dedea31b66cf4159920cd0fc76eb31df
Source dataset
uspto-grants-2007_06
Patent number
US07232902B2

Reaction notes

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