Diethyl Ether → HCID 18668009, compound

HRID 990575Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:14][CH2:13][CH:12]([N:15]([CH3:17])[CH3:16])[CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C[I:19].[CH2:20](OCC)C>CN(C)C=O>[I-:19].[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:14][CH2:13][CH:12]([N+:15]([CH3:20])([CH3:17])[CH3:16])[CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of [1-(4-nitrophenyl)-pyrrolidin-3-yl] dimethylamine (470 mg, 2.0 mmole) in dimethylforamide (2 mL) was added methyl iodide (567 mg., 4.0 mmole). The reaction mixture was stirred at 60° C. for 18 hrs and cooled to room temperature. Diethyl ether was added and the resulting precipitate was filtered and washed with ether three times to give 1-(4-nitrophenyl)-N,N,N-trimethylpyrrolidin-3-aminium iodide (894 mg, 92% yield): 1HNMR (400 MHz, DMSO-d6)δ 2.50 (m, 2H), 3.15 (s, 9H), 3.43 (m, 1H), 3.71 (m, 2H), 3.87 (m, 1H), 4.37 (m, 1H), 6.74 (d, 2H, J=9 Hz), 8.12(d, 2H, J=9 Hz). This compound was hydrogenated at 60 psi in menthol in the presence of 10% Pd/C at room temperature for about 18 hrs. The reaction mixture was filtered through a pad of Celite and washed with methanol. The filtrate was evaporated in vacuo to produce 1-(4-aminophenyl)-N,N,N-trimethylpyrrolidin-3-aminium iodide (505 mg, 95% yield): 1HNMR (400 MHz, DMSO-d6)δ 2.32 (m, 2H), 2.94 (m, 1H), 3.09 (s, 9H), 3.17 (m, 2H), 3.71 (m, 2H), 4.25 (m, 1H), 4.66 (bs, 2H), 6.52 (s, 4H): MS m/z=219. This is Compound 1 of Table 1.

Workup

temperaturecooled to room temperature
filtrationthe resulting precipitate was filtered
washwashed with ether three times

Sources & evidence

ORD record: ord-e0443a06286c45fcabbbe780fe4f761e
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06461391B1

Reaction notes

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