Ethyl Bromide → HCID 20494483, compound

HRID 1577895Notes

Reaction equation

HRID 1577895 reaction equation
[CH2:1]([N:3]([CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH3:2].[CH2:23]([Br:25])[CH3:24]>>[Br-:25].[CH2:1]([N+:3]([CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=1)([CH2:23][CH3:24])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH3:2]

Participants

3

Reactant 2

HCID 6332Ethyl BromideHCID 20570202HCID 20570202, compound

Product 1

HCID 20494483HCID 20494483, compound

Procedure

24 Grams of N-ethyl-N-n-heptyl-4-(4-methoxyphenyl)butylamine was placed in a 500 ml. round bottom flask and 200 ml. ethyl bromide was added. The mixture was refluxed for 31/2 days. Thin layer chromatography indicated very little secondary amine left. The excess ethyl bromide was evaporated in vacuo leaving an oil, N,N-diethyl-N-n-heptyl-4(4-methoxyphenyl)butylammonium bromide which next was converted to the hydroxide form as follows: Using 350 ml. BIO-RAD, hydroxide form, 100-200 mesh 1.2 meq./ml. resin in a water packed column the oil was taken up in water and flushed over the column. 800 Milliters was collected off the column. This was partly acidified from pH 12.4 to pH 10 with 15 g. of p-toluenesulfonic acid in water. The solution tended to oil on acidification. This suspension was passed over a column of 300 ml. of resin which had been converted to the tosylate form by washing with 1 l. of 0.4 N p-toluenesulfonic acid solution. A total of 4 l. eluate was collected. Lyophilization of the eluate for 11/2 days left a residue which was taken up in hot ethyl acetate, filtered and evaporated in vacuo. 44 Grams of oil was left which solidified on standing. The material was recrystallized from 300 ml. ethyl acetate to form 36.76 g. N,N-diethyl-N-n-heptyl-4(4-methoxyphenyl)butylammonium p-toluenesulfonate. M.P. 65°-67° C.

Workup

  1. temperatureThe mixture was refluxed for 31/2 days
  2. waitleft
  3. customThe excess ethyl bromide was evaporated in vacuo

Sources & evidence

ORD record
ord-384a4c124f974a0d8628edb44d8e68b7
Source dataset
uspto-grants-1981_09
Patent number
US04289787

Reaction notes

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