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

HRID 63022Notes

Reaction equation

HRID 63022 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH:15]=O)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[CH2:19]([N:21]([CH2:25][CH3:26])[CH2:22][CH2:23][NH2:24])[CH3:20]>[Pd].C1(C)C=CC=CC=1>[CH2:19]([N:21]([CH2:25][CH3:26])[CH2:22][CH2:23][NH:24][CH2:15][C:12]1[CH:13]=[CH:14][C:9]([C:6]2[CH:7]=[CH:8][C:3]([C:2]([F:18])([F:17])[F:1])=[CH:4][CH:5]=2)=[CH:10][CH:11]=1)[CH3:20]

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-diamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 4′-(trifluoromethyl)-4-biphenylcarbaldehyde, (43.6 kg, 1.1 eq., see WO 01/60805), N,N-diethylethylenediamine (21.2 kg, 1.15 equiv.) and 5% palladium on charcoal (Degussa E101 N/W, 50% wet paste, 1.7 kg) in toluene (138 Kg) was hydrogenated at 20±3° C. and 50 psi until completion. The reaction mixture was filtered and the catalyst bed washed with toluene (2×36.7 kg). The solution was washed with water (84.8 kg) and concentrated under reduced pressure to ca. 85 L. This concentrate was used in the next step, Example 6, without further purification.

Workup

  1. customwas hydrogenated at 20±3° C.
  2. filtrationThe reaction mixture was filtered
  3. washthe catalyst bed washed with toluene (2×36.7 kg)
  4. washThe solution was washed with water (84.8 kg)
  5. concentrationconcentrated under reduced pressure to ca. 85 L
  6. customThis concentrate was used in the next step, Example 6, without further purification

Sources & evidence

ORD record
ord-2c0c0c7a006e4282b0270b4e07b3c34b
Source dataset
uspto-grants-2016_09
Patent number
US09447052B2

Reaction notes

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