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

HRID 2374750Notes

Reaction equation

HRID 2374750 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:16]=[CH:15][C:12]([CH:13]=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].[BH4-].[Na+].[H][H]>ClCCl.C(O)C>[CH2:19]([N:21]([CH2:25][CH3:26])[CH2:22][CH2:23][NH:24][CH2:13][C:12]1[CH:15]=[CH:16][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

7

Reactant 4

HCID 60993N,N-DiethylethylenediamineHCID 27827124'-(Trifluoromethyl)-4-biphenylcarbaldehydeHCID 4311764Sodium borohydrideHCID 178418361HCID 178418361, compound

Product 1

HCID 11233414N,N-Diethyl-N'-(4'-trifluoromethylbiphenyl-4-ylmethyl)-ethane-1,2-diamineYield 98%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

4-(4-Trifluoromethylphenyl)benzaldehyde (85.43 g, 0.3414 mol) (Int. D2) and 4A molecular sieve (400 g, predried at 120° C.) were suspended in dichloromethane (1.4 L), then N,N-diethylethylenediamine (47.97 ml, 0.3414 mol) was added. The mixture was left at room temperature for 16 h with occasional shaking, then the sieves were filtered off and washed with dichloromethane. The combined filtrates were evaporated to a yellow solid and dried under high vacuum. This material (114.3 g, 0.328 mol) in ethanol (1 L) was cooled in an ice bath, and sodium borohydride (12.41 g, 0.328 mol) was added under argon with stirring. Hydrogen evolution was observed. After 30 min the ice bath was removed, and the cloudy yellow solution was left to stand at room temperature for 16 h. The solvent was removed in vacuo, water and brine were added, and the mixture was extracted 3× with dichloromethane. The combined extracts were dried over potassium carbonate and evaporated to give the title compound as a yellow solid, (112.1 g, 98%). 1H-NMR (CDCl3) δ 7.66 (4H, s), 7.53-7.56 (2H, m), 7.40-7.44 (2H, m), 3.86 (2H, s), 2.47-2.75 (9H, m), 0.96-1.10 (6H, m); MS(APCI+) found (M+1)=351, C20H25F3N2 requires 350.

Workup

  1. filtrationthe sieves were filtered off
  2. washwashed with dichloromethane
  3. customThe combined filtrates were evaporated to a yellow solid
  4. customdried under high vacuum
  5. customAfter 30 min the ice bath was removed
  6. waitthe cloudy yellow solution was left
  7. waitto stand at room temperature for 16 h
  8. customThe solvent was removed in vacuo, water and brine
  9. additionwere added
  10. extractionthe mixture was extracted 3× with dichloromethane
  11. dry with materialThe combined extracts were dried over potassium carbonate
  12. customevaporated

Sources & evidence

ORD record
ord-12a23c56b9c94989be821409bf647c8a
Source dataset
uspto-grants-2008_12
Patent number
US07462620B2

Reaction notes

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