Acetic Acid → N-(6-Bromo-indan-2-yl)-N-propyl-propionamide

HRID 725916Notes

Reaction equation

HRID 725916 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[N:10]([CH2:15][CH2:16][CH3:17])[C:11](=[O:14])[CH2:12][CH3:13].C(O)(=O)C.[Br:22]Br>ClCCl>[Br:22][C:7]1[CH:8]=[C:9]2[C:4]([CH2:3][CH:2]([N:10]([CH2:15][CH2:16][CH3:17])[C:11](=[O:14])[CH2:12][CH3:13])[CH2:1]2)=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24408Bromine3×HCID 19710204N-Indan-2-yl-N-propyl-propionamide

Product 1

HCID 19710191N-(6-Bromo-indan-2-yl)-N-propyl-propionamideYield 34%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-Indan-2-yl-N-propyl-propionamide (Preparation 13, 1 g, 4.32 mmol) was dissolved in dichloromethane (100 mL). Glacial acetic acid was added to adjust the pH to 4. This was followed by the addition of bromine (0.4 ml, 7.78 mmol). The solution was stirred at room temperature for 8 h. Additional bromine (0.2 ml, 3.89 mmol) was added and the solution was refluxed for 18 h. Since the reaction was not complete another portion of bromine (0.2 ml, 3.89 mmol) was added and the reaction mixture was refluxed for another 4 h. The organic layer was extracted with aqueous Na2CO3 (10%) and the layers were separated. The organic layer was dried (MgSO4). The solvent was evaporated and the remaining crude product was chromatographed (SiO2) with n-hexane:ethyl acetate (4:1) as eluant. The pure fractions were pooled yielding 0.45 g (34%) of N-(6-Bromo-indan-2-yl)-N-propyl-propionamide. 1H NMR (300 MHz, CDCl3) δ 0.85 (t, 3H), 1.15 (t, 3H), 1.50-1.65 (m, 2H), 2.30-2.50 (m, 2H), 2.90-3.25 (m, 6H), 4.70-5.10 (m, 1H), 7.00-7.10 (t, 1H), 7.25-7.40 (m, 2); MS m/e 309 (1, M+), 116 (100), 115 (92), 194 (57), 196 (55).

Workup

  1. temperaturethe solution was refluxed for 18 h
  2. additionwas added
  3. temperaturethe reaction mixture was refluxed for another 4 h
  4. extractionThe organic layer was extracted with aqueous Na2CO3 (10%)
  5. customthe layers were separated
  6. dry with materialThe organic layer was dried (MgSO4)
  7. customThe solvent was evaporated
  8. customthe remaining crude product was chromatographed (SiO2) with n-hexane:ethyl acetate (4:1) as eluant

Sources & evidence

ORD record
ord-684f883d6cbe4b9c9075f642c03427a0
Source dataset
uspto-grants-1998_01
Patent number
US05708018

Reaction notes

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