Methyl iodide → HCID 66986938, compound

HRID 556018Notes

Reaction equation

[CH3:1][C:2]([N+:10]([O-:12])=[O:11])([CH3:9])[CH2:3][N:4]1[CH2:8][CH2:7][CH2:6][CH2:5]1.[CH3:13][I:14]>C1(C)C=CC=CC=1>[I-:14].[CH3:13][N+:4]1([CH2:3][C:2]([CH3:1])([N+:10]([O-:12])=[O:11])[CH3:9])[CH2:8][CH2:7][CH2:6][CH2:5]1

Participants

Conditions

Temperature: 80 °C

Procedure

Here, N-methyl-N-(2-methyl-2-nitro-propyl)-pyrrolidinium iodide was prepared by dissolving N-(2-methyl-2-nitro-propyl)-pyrrolidine (70 g, 0.4 mol) in toluene (100 mls), and thereafter under ice bath conditions adding drop wise methyl iodide (58 g, 26 mls, 0.41 mol) in toluene (70 mls) over a period of time of 30 minutes. After the addition was complete, the ice bath was removed and the solution was heated to a temperature of 80° C. A white solid was observed to precipitate. Stirring and heating were continued for an additional period of time of 6 hours. The white precipitate was recovered by filtration, and thereafter washed first with acetone (100 mls) and then with diethyl ether (50 mls) to yield after air drying 83 grams (65%), FTIR: (KBr, cm−1) 3026, 2978, 2874, 1544, 1492, 1475, 1459, 1439, 1377, 1344, 1307, 1229, 1195, 1152, 1052, 1012, 997, 926, 852, 833. 1H NMR (60 MHz, CDCl3/DMSO-d6, ref TMS, ppm) 1.85 (s, 6H) 2.1-2.3 (m, br, 4H) 2.96 (s, 2H) 3.9-3.7 (m, br, 4H) 4.45 (s, 3H). Elemental

Workup

additionAfter the addition
customthe ice bath was removed
customto precipitate
temperatureheating
filtrationThe white precipitate was recovered by filtration
washwashed first with acetone (100 mls)
customwith diethyl ether (50 mls) to yield after air
customdrying 83 grams (65%), FTIR

Sources & evidence

ORD record: ord-c9849bc8ac8d4227bc16393ac4a4fa4d
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08053589B1

Reaction notes

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