1-Bromohexane → N-(4-Aminophenyl)-N-hexylacetamide

HRID 1983567

Reaction equation

HRID 1983567 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([NH:6][C:7](=[O:9])[CH3:8])=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>CN(C)C=O>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([N:6]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:7](=[O:9])[CH3:8])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 81011-BromohexaneHCID 24758Sodium hydrideHCID 312304-Aminoacetanilide

Product 1

HCID 57713043N-(4-Aminophenyl)-N-hexylacetamideYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4′-aminoacetanilide (1.00 g, 6.66 mmol) in N,N-dimethylformamide (10 mL) was added sodium hydride (60% dispersion in mineral oil; 0.28 g, 7.0 mmol). After 5-10 minutes, 1-bromohexane was added dropwise to the mixture. The reaction was stirred for one hour and then partitioned between ethyl acetate and water. The organic layer was washed with additional water, dried (sodium sulfate) and concentrated. The resulting brown oil was purified by flash chromatography over silica (methylene chloride/methanol) to afford 1.32 g (84%) of product as a viscous amber oil: 1H NMR (CDCl3) δ 6.91 (d, J=8.7 Hz, 1H), 6.68 (d, J=8.7Hz, 1H), 3.78 (br s, 2H), 3.61 (t, J=7.9Hz, 2H), 1.81 (s, 3H), 1.33-1.18 (m, 2H), 1.17-1.08 (m, 6H), 0.85 (t, J=6.9 Hz, 3H) ppm.

Workup

  1. custompartitioned between ethyl acetate and water
  2. washThe organic layer was washed with additional water
  3. dry with materialdried (sodium sulfate)
  4. concentrationconcentrated
  5. customThe resulting brown oil was purified by flash chromatography over silica (methylene chloride/methanol)

Sources & evidence

ORD record
ord-35b4111d6cad4ddbabfc43a67b491af2
Source dataset
uspto-grants-2009_06
Patent number
US07541466B2

Linked notes

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