1-Bromo-3-methylbutane → HCID 18469928, compound

HRID 2228468Notes

Reaction equation

HRID 2228468 reaction equation
[CH:1]1([N:11]2[CH2:17][CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.Br[CH2:26][CH2:27][CH:28]([CH3:30])[CH3:29]>C1COCC1>[CH:1]1([N:11]2[CH2:17][CH2:16][CH2:15][N:14]([CH2:26][CH2:27][CH:28]([CH3:30])[CH3:29])[CH2:13][CH2:12]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 78911-Bromo-3-methylbutaneHCID 8471TriethylamineHCID 11287680HCID 11287680, compound

Product 1

HCID 18469928HCID 18469928, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 250 mL flask was charged with a solution of 1-(1,2,3,4-tetrahydronaphthyl)homopiperazine (2.68 g, 11.6 mmol) in THF (105 mL). Triethylamine (2.20 ml, 3.03 g, 29.9 mmol) and 1-bromo-3-methylbutane (2.00 ml, 1.59 g, 10.5 mmol) were added. The solution was immersed in a 60° C. oil bath for 16 hours during which time a precipitate formed. The resulting mixture was filtered and the filtrate was concentrated to give an orange oil. This crude product was purified by column chromatography using diethyl ether:hexane:methanol (5:5:1) to obtain the title compound as a yellow oil (2.34 g). 1H NMR (CDCl3, 300 MHz) δ 0.89 (d, 6H), 1.39 (m, 2H), 1.54-1.79 (m, 5H), 1.92-2.15 (m, 2H), 2.50 (m, 2H), 2.60-2.80 (m, 10H), 3.90 (m, 1H), 7.02-7.18 (m, 3H), 7.77 (d, 2H); m/s: M+H+ 301.

Workup

  1. customwas immersed in a 60° C.
  2. customfor 16 hours
  3. customformed
  4. filtrationThe resulting mixture was filtered
  5. concentrationthe filtrate was concentrated
  6. customto give an orange oil
  7. customThis crude product was purified by column chromatography

Sources & evidence

ORD record
ord-16cc7bf0e15942fca7d0c08146895486
Source dataset
uspto-grants-2002_07
Patent number
US06417183B1

Reaction notes

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