Dimethylamine → Methyl 4-[3-(dimethylamino)-propyl]benzoate

HRID 131295Notes

Reaction equation

S(O[CH2:12][CH2:13][CH2:14][C:15]1[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=1)(C1C=CC(C)=CC=1)(=O)=O.[CH3:25][NH:26][CH3:27]>CN(C)C=O.O1CCCC1.C(OCC)(=O)C>[CH3:25][N:26]([CH3:27])[CH2:12][CH2:13][CH2:14][C:15]1[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of methyl 4-(3-tosyloxypropyl)benzoate (500 mg) in dimethylformamide (3 mL) is added 2M dimethylamine solution in tetrahydrofuran (2.2 mL) and the mixture is stirred at 50° C. for 15 hours. The reaction mixture is diluted with ethyl acetate, washed with a saturated sodium hydrogencarbonate solution and concentrated in vacuo. The residue is purified by column chromatography on silica gel (Solvent; chloroform:methanol=100:0→90:10) to give methyl 4-[3-(dimethylamino)-propyl]benzoate (357 mg, yield; quantitative) as an oil. MS (APCI) m/z; 222 [M+H]+

Workup

washwashed with a saturated sodium hydrogencarbonate solution
concentrationconcentrated in vacuo
customThe residue is purified by column chromatography on silica gel (Solvent; chloroform:methanol=100:0→90:10)

Sources & evidence

ORD record: ord-f8dae7f71a66436181b2ae415cfec5e5
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07384952B2

Reaction notes

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