tert-Butyl 4-n-octylphenyl(methyl)carbamate → N-methyl-4-octylaniline

HRID 717626Notes

Reaction equation

HRID 717626 reaction equation
[CH2:1]([C:9]1[CH:14]=[CH:13][C:12]([N:15](C)[C:16](=O)OC(C)(C)C)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]>C(O)(C(F)(F)F)=O.C(Cl)Cl.CCO.Cl>[CH3:16][NH:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:10][CH:11]=1

Participants

6

Reactant 1

HCID 66615053tert-Butyl 4-n-octylphenyl(methyl)carbamate

Product 1

HCID 17827013N-methyl-4-octylanilineYield 57%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of the product of Step A (0.14 g; 0.44 mmol) in 60% TFA in CH2Cl2 (5 ml) was stirred for 30 min at room temperature and the mixture was diluted to 5 ml with EtOH and a few drops of concentrated HCl was added. This was evaporated to dryness under reduced pressure, kept in vacuo for 1 h and the residue was partitioned between saturated NaHCO3 (5 ml) and Et2O (15 ml). The organic phase was dried over anhydrous MgSO4 and filtered. The filtrate was evaporated under reduced pressure and the residue was purified by FCC (SiO2, hexane/EtOAc 9:1) to give the title compound (0.055 g; 57%), as a creamy solid. 1H-NMR (CDCl3) 7.01 (d, 2H, J=8.2 Hz); 6.55 (d, 2H, J=8.2 Hz); 3.55 (broad s, 1H); 2.81 (s, 3H); 2.49 (t, 2H, J=7.9 Hz); 1.56 (m, 2H); 1.28 (m, 10H); 0.88 (t, 3H, J=6.8 Hz).

Workup

  1. additionwas added
  2. customThis was evaporated to dryness under reduced pressure
  3. customthe residue was partitioned between saturated NaHCO3 (5 ml) and Et2O (15 ml)
  4. dry with materialThe organic phase was dried over anhydrous MgSO4
  5. filtrationfiltered
  6. customThe filtrate was evaporated under reduced pressure
  7. customthe residue was purified by FCC (SiO2, hexane/EtOAc 9:1)

Sources & evidence

ORD record
ord-b87d06603e2e4515a266acc7b598dab6
Source dataset
uspto-grants-2015_11
Patent number
US09193716B2

Reaction notes

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