Sodium Hydroxide → (6-Bromo-indan-2-yl)-dipropyl-amine

HRID 725920Notes

Reaction equation

HRID 725920 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-].[Br:11][C:12]1[CH:20]=[C:19]2[C:15]([CH2:16][CH:17]([N:21]([CH2:26][CH2:27][CH3:28])[C:22](=O)[CH2:23][CH3:24])[CH2:18]2)=[CH:14][CH:13]=1.[OH-].[Na+]>C1COCC1>[Br:11][C:12]1[CH:20]=[C:19]2[C:15]([CH2:16][CH:17]([N:21]([CH2:26][CH2:27][CH3:28])[CH2:22][CH2:23][CH3:24])[CH2:18]2)=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 19710191N-(6-Bromo-indan-2-yl)-N-propyl-propionamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 21221814(6-Bromo-indan-2-yl)-dipropyl-amineYield 83.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-15 °C

Procedure

Lithium aluminium hydride (90 mg, 2.36 mmol) and aluminium chloride (350 mg, 2.25 mmol) were added to dry THF (25 mL). The mixture was cooled to -15° C. and kept at this temperature for 15 min. N-(6-Bromo-indan-2-yl)-N-propyl-propionamide (preparation 14, 0.35 g, 1.13 mmol) dissolved in dry THF (10 mL) was added and the reaction mixture was stirred at -15° C. for 90 min. Aqueous NaOH (15 mL, 15%) was added and the mixture extracted with ethyl acetate. The layers were separated and the organic layer washed with water, dried (Na2CO3) and the solvent was evaporated to dryness. The crude product was chromatographed and the pure fractions were pooled, yielding 280 mg (83%) of (6-bromo-indan-2-yl)-dipropyl-amine as the free base. The amine was converted to its hydrochloride salt with EtOH-HCl and recrystallized from a mixture of 2-propanol and isopropyl ether. m.p. 196°-198° C. (HCl); 1H NMR (300 MHz, CDCl3) δ 0.90 (t, 6H), 1.50 (m, 4H), 2.50 (t, 4H), 2.75-3.08 (m, 4H), 3.60-3.75 (p, 1H), 7.05 (d, J=8 Hz, 1H), 7.28 (d, J=8 Hz, 1H), 7.32 (s, 1H); 13C NMR (75.4 MHz, CDCl3) δ 12.02, 20.30, 36.25, 36.62, 53.39, 63.25, 119.82, 125.95, 127.56, 129.26, 141.00, 144.47; MS m/e 295 (6, M+), 269 (100), 266 (98), 116 (54), 115 (41).

Workup

  1. additionwas added
  2. extractionthe mixture extracted with ethyl acetate
  3. customThe layers were separated
  4. washthe organic layer washed with water
  5. dry with materialdried (Na2CO3)
  6. customthe solvent was evaporated to dryness
  7. customThe crude product was chromatographed

Sources & evidence

ORD record
ord-afa08ccefa6649f18a9410a927ad2ffd
Source dataset
uspto-grants-1998_01
Patent number
US05708018

Reaction notes

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