4-Methylpyridine → HCID 22482768, compound

HRID 2181777Notes

Reaction equation

[Br:1][CH2:2][CH2:3][CH2:4][OH:5].[N:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1>C(O)C>[Br-:1].[OH:5][CH2:4][CH2:3][CH2:2][N+:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Anhydrous ethanol (250 mL) was added to a two-neck, 1 L round-bottomed flask, flushed with nitrogen, followed by addition of 3-bromo-1-propanol (60.0 g, 0.4317 mol) and 4-picoline (43.8 g, 0.4701 mol). The mixture was heated with stirring at 60° C. for 24 hours under nitrogen. The reaction was stopped and the contents in flask were transferred to a one-neck round-bottomed flask. The solvent was removed under vacuum leaving the product as a viscous, dark yellow-orange liquid. The product was washed within the same flask with diethyl ether (4×100 mL) and any remaining solvent was removed under vacuum. The yield of N-(3-hydroxypropyl)-4-picolinium bromide was 96.6 g (96% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.98 (2H, d, J=6.8 Hz), 8.00 (2H, d, J=6.8 Hz), 4.64 (2H, t, J=7.0 Hz, 7.0 Hz), 3.44 (2H, t, J=6.0 Hz, 6.0 Hz), 2.62 (3H, s), 2.06 (2H, p, J=6.8 Hz, 6.0 Hz, 6.0 Hz, 6.8 Hz). IR (neat): 3332 cm−1 (O—H), 1642 cm−1 (>C═N—C), 1518 cm−1 (C—C aromatic).

Workup

customflushed with nitrogen
temperatureThe mixture was heated
customthe contents in flask were transferred to a one-neck round-bottomed flask
customThe solvent was removed under vacuum
customleaving the product as a viscous, dark yellow-orange liquid
washThe product was washed within the same flask with diethyl ether (4×100 mL)
customany remaining solvent was removed under vacuum

Sources & evidence

ORD record: ord-a39a162d57fe4d0d972737c37ae00144
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06894169B1

Reaction notes

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