Benzhydrylamine → HCID 178446320, compound

HRID 537381Notes

Reaction equation

HRID 537381 reaction equation
C(OC(N[C@H:9]([C:13]([CH2:17]C)([CH3:16])[CH2:14][CH3:15])[C:10](O)=O)=O)(C)(C)C.[O-]S([O-])(=O)=O.[Na+].[Na+].[NH2:26][CH:27]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C(Cl)Cl>[CH2:9]([C:13]([CH3:17])([CH2:14][CH3:15])/[CH:16]=[N:26]/[CH:27]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH3:10]

Participants

5

Reactant 3

HCID 7036BenzhydrylamineHCID 24436Sodium SulfateHCID 86678254HCID 86678254, compound

Product 1

HCID 178446320HCID 178446320, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 100-mL round-bottomed flask containing crude 2-ethyl-2-methylbutanal (15) was charged with CH2Cl2 (20 mL) and Na2SO4 (10 g). Aminodiphenylmethane (9) (8.83 mL, 80 mmol, 0.80 equiv) was added via syringe. The flask was capped with a plastic stopper, and the mixture was stirred at room temperature for 14 h. The reaction mixture was filtered through a medium porosity fritted disk funnel and rinsed with CH2Cl2 (4×10 mL). The filtrate was concentrated under reduced pressure and maintained at 1 torr with stirring for 1 h to provide a slightly cloudy, colorless oil. A 5-cm diameter fritted disk funnel was filled with a 3-cm high layer of silica gel. The funnel was rinsed with a solution of 20:1:0.5 hexanes/Et2O/triethylamine (50 mL) under reduced pressure, followed by a solution of 20:1 hexanes/Et2O (50 mL). The oil prepared above was dissolved in 20:1 hexanes/Et2O (25 mL) and rinsed through the frit into a 250-mL round-bottomed flask under reduced pressure, rinsing with 20:1 hexanes/Et2O (4×25 mL). The mixture was concentrated under reduced pressure (30 torr→1 torr) to provide a clear, colorless oil that was slightly cloudy. The oil was maintained at 1 torr for 1 h while stirring to provide (E)-N-(2-ethyl-2-methylbutylidene)diphenylmethanamine (2b) in 95% 1H-NMR purity. Yield: 18.7 g (67 mmol, 84% from aminodiphenylmethane, 67% from 2-ethyl-2-butanal).

Workup

  1. customThe flask was capped with a plastic stopper
  2. filtrationThe reaction mixture was filtered through a medium porosity fritted disk funnel
  3. washrinsed with CH2Cl2 (4×10 mL)
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. temperaturemaintained at 1 torr
  6. stirringwith stirring for 1 h
  7. customto provide a slightly cloudy, colorless oil
  8. additionA 5-cm diameter fritted disk funnel was filled with a 3-cm high layer of silica gel
  9. washThe funnel was rinsed with a solution of 20:1:0.5 hexanes/Et2O/triethylamine (50 mL) under reduced pressure
  10. customThe oil prepared
  11. washrinsed through the frit into a 250-mL round-bottomed flask under reduced pressure
  12. washrinsing with 20:1 hexanes/Et2O (4×25 mL)
  13. concentrationThe mixture was concentrated under reduced pressure (30 torr→1 torr)
  14. customto provide a clear, colorless oil that
  15. temperatureThe oil was maintained at 1 torr for 1 h
  16. stirringwhile stirring

Sources & evidence

ORD record
ord-acd62c9514414d5f8bf6f94b5b51651b
Source dataset
uspto-grants-2014_10
Patent number
US08859812B2

Reaction notes

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