Dimethylformamide → Dimethylheptyl(1-hydroxy-p-menth-2-yl)ammonium bromide

HRID 1657330Notes

Reaction equation

[CH3:1][N:2]([CH3:14])[CH:3]1[CH2:8][CH:7]([CH:9]([CH3:11])[CH3:10])[CH2:6][CH2:5][C:4]1([OH:13])[CH3:12].[CH2:15]([Br:22])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]C.[CH3:23]N(C)C=O>O>[Br-:22].[CH3:14][N+:2]([CH3:23])([CH2:1][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH:3]1[CH2:8][CH:7]([CH:9]([CH3:11])[CH3:10])[CH2:6][CH2:5][C:4]1([OH:13])[CH3:12]

Participants

Conditions

Temperature: 90 °C

Procedure

Five grams of 2-dimethylamino-1-p-menthanol and 10 g. of heptyl bromide were dissolved in 5 ml. of dimethylformamide. The solution was warmed at 90°C (under nitrogen) for 16 hours, cooled to room temperature and diluted with water (approximately 100 ml.). The mixture was transferred to a separatory funnel and washed three times with ethyl ether (20-25 ml.). The neutral, aqueous phase was concentrated to dryness on a film evaporator (at 50°C). Ninety-five percent ethanol was added to the flask contents to assist the azeotropic removal of water. Last traces of DMF were removed at high vacuum (1 mm.). Yield of dimethyl heptyl (1-hydroxy-p-menthan-2-yl) ammonium bromide was 10.2 g. (100T of theory).

Workup

temperaturecooled to room temperature
customThe mixture was transferred to a separatory funnel
washwashed three times with ethyl ether (20-25 ml.)
concentrationThe neutral, aqueous phase was concentrated to dryness on a film evaporator (at 50°C)
additionNinety-five percent ethanol was added to the flask contents
customthe azeotropic removal of water
customLast traces of DMF were removed at high vacuum (1 mm.)

Sources & evidence

ORD record: ord-a1e4fbf499da4448b9e3bbfc581a6fc8
Source dataset: uspto-grants-1976_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03960539

Reaction notes

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