1-Bromopentane → 4-Bromo-3-chloro-N,N-dipentylaniline

HRID 1250004Notes

Reaction equation

HRID 1250004 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[Br:7][C:8]1[CH:14]=[CH:13][C:11]([NH2:12])=[CH:10][C:9]=1[Cl:15].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH2:2]([N:12]([CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[C:11]1[CH:13]=[CH:14][C:8]([Br:7])=[C:9]([Cl:15])[CH:10]=1)[CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 3

HCID 80571-BromopentaneHCID 11430Potassium CarbonateHCID 888884-Bromo-3-chloroaniline

Product 1

HCID 183293124-Bromo-3-chloro-N,N-dipentylanilineYield 106.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1-Bromopentane (0.42 mL, 3.4 mmol) was added to a mixture of 4-bromo-3-chloroaniline (200 mg, 0.9 mmol) and potassium carbonate (199 mg, 1.4 mmol) in DMF (20 mL) and the reaction was heated to 13 0˜˜C overnight. The mixture was cooled, diluted with water (20 mL) and extracted with petroleum ether (3×25mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified via flash column chromatography using 9:1 petroleum ether:ethyl acetate as eluent to give N,N-Dipentyl-4-bromo-3-chloroaniline (1) (332 mg, 68%). 1HNMR (CDCI3) 67.02 (d, IH, ArH); 3.12 (t, 4H, 2×NCH2); 0.95 (t, 6H, 2×CH3). MS; 347 (M+H).

Workup

  1. temperaturethe reaction was heated to 13 0˜˜C overnight
  2. temperatureThe mixture was cooled
  3. extractionextracted with petroleum ether (3×25mL)
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified via flash column chromatography

Sources & evidence

ORD record
ord-d25a5bcc6d6e468e9ad3ba3787307468
Source dataset
uspto-grants-2002_01
Patent number
US06335446B1

Reaction notes

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