Triethylamine → Methyl 3-methyl-5-{[methyl(pentyl)amino]methyl}benzoate

HRID 14136Notes

Reaction equation

HRID 14136 reaction equation
O[CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([CH3:13])[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7].C(N(CC)CC)C.CS(Cl)(=O)=O.[CH3:26][NH:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]>C(Cl)Cl>[CH3:13][C:11]1[CH:10]=[C:5]([CH:4]=[C:3]([CH2:2][N:27]([CH3:26])[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 117479N-MethylpentylamineHCID 21086184Methyl 3-(hydroxymethyl)-5-methylbenzoate

Product 1

HCID 21086189Methyl 3-methyl-5-{[methyl(pentyl)amino]methyl}benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice-cold, stirred solution of methyl 3-(hydroxymethyl)-5-methylbenzoate (200 mg, 1.1 mmol) in methylene chloride (2.2 mL) is added triethylamine (0.304 mL, 2.2 mmol) followed by methanesulfonyl chloride (0.116 mL, 1.5 mmol). The reaction mixture is stirred for 15 min and filtered. N-Methylpentylamine (333 mg, 3.3 mmol) is added to the filtrate, and the reaction mixture is stirred at room temperature for 5 h. The reaction mixture is diluted with methylene chloride (10 mL), washed with 1 N hydrochloric acid, and saturated sodium bicarbonate, dried (magnesium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 15% ethyl acetate/hexanes) provides the title compound. 1H NMR (300 MHz, CDCl3) δ 7.75 (d, J=4 Hz, 2H), 7.36 (s, 1H), 3.90 (s, 3H), 3.47 (s, 2H), 3.13 (t, J=9 Hz, 3H), 2.39 (s, 2H), 2.34 (d, J=8 Hz, 2H), 2.18 (s, 3H), 1.45 (m, 5H), 1.32 (m, 2H).

Workup

  1. filtrationfiltered
  2. stirringthe reaction mixture is stirred at room temperature for 5 h
  3. washwashed with 1 N hydrochloric acid, and saturated sodium bicarbonate
  4. dry with materialdried (magnesium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by flash column chromatography (silica, 15% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-3d2ea35b943343e0ad8cefcd218ac4a0
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Reaction notes

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