Benzhydrylamine → HCID 10729452, compound

HRID 537376Notes

Reaction equation

HRID 537376 reaction equation
[O-]S([O-])(=O)=O.[Na+].[Na+].[CH3:8][C:9]([CH3:13])([CH3:12])[CH:10]=O.[NH2:14][CH:15]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(Cl)Cl>[CH3:8][C:9]([CH3:13])([CH3:12])[CH:10]=[N:14][CH:15]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 7036BenzhydrylamineHCID 12417PivalaldehydeHCID 24436Sodium Sulfate

Product 1

HCID 10729452HCID 10729452, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 100-mL round-bottomed flask containing a stir bar was charged with Na2SO4 (8.0 g) and CH2Cl2 (40 mL). Trimethylacetaldehyde (8) (7.65 mL, 52 mmol, 1.3 equiv) and aminodiphenylmethane (9) (6.89 mL, 40 mmol, 1.0 equiv) were added sequentially via syringe while stirring. The flask was capped with a plastic stopper, and the mixture was stirred at room temperature. The mixture became cloudy after 5 min. After stirring for 1 h, the solution was decanted into a 200-mL round-bottomed flask, rinsing with CH2Cl2 (4×5 mL) and concentrated to 8-10 mL using a rotary evaporator. The flask was then maintained at 1 torr for 10 min. A 5-cm diameter fritted disk funnel was filled with a 2-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 tared 250-mL round-bottomed flask under reduced pressure, rinsing with 20:1 hexanes/Et2O (4×25 mL). The mixture was concentrated (30 torr→1 torr) to provide a clear, pale yellow oil that solidified into a white solid. The solid was broken up into approximately 1-cm diameter pieces using a spatula, and was maintained at 1 torr for another 15 min to provide N-(2,2-dimethyl propylidene)diphenylmethanamine (2a) as a white solid in approximately 98% 1H-NMR purity. The product was used in the next step without further purification. Yield: 9.93 g (39.6 mmol, 99%).

Workup

  1. additionA 100-mL round-bottomed flask containing a stir bar
  2. customThe flask was capped with a plastic stopper
  3. stirringthe mixture was stirred at room temperature
  4. customafter 5 min
  5. stirringAfter stirring for 1 h
  6. customthe solution was decanted into a 200-mL round-bottomed flask
  7. washrinsing with CH2Cl2 (4×5 mL)
  8. concentrationconcentrated to 8-10 mL
  9. customa rotary evaporator
  10. temperatureThe flask was then maintained at 1 torr for 10 min
  11. additionA 5-cm diameter fritted disk funnel was filled with a 2-cm high layer of silica gel
  12. washThe funnel was rinsed with a solution of 20:1:0.5 hexanes/Et2O/triethylamine (50 mL) under reduced pressure
  13. customThe oil prepared
  14. washrinsed through the frit into a tared 250-mL round-bottomed flask under reduced pressure
  15. washrinsing with 20:1 hexanes/Et2O (4×25 mL)
  16. concentrationThe mixture was concentrated (30 torr→1 torr)
  17. customto provide a clear, pale yellow oil
  18. temperaturewas maintained at 1 torr for another 15 min

Sources & evidence

ORD record
ord-ca79f36c4b704ae5abf7cdd6502db4fa
Source dataset
uspto-grants-2014_10
Patent number
US08859812B2

Reaction notes

Loading…