Methanesulfonic Acid → 1-(3,5-Bistrifluoromethylphenyl)-3-(4-tert-butylpiperidino)prop-1-yne methanesulphonate

HRID 67926Notes

Reaction equation

HRID 67926 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:4]=[C:5]([C:13]#[C:14][CH2:15][N:16]2[CH2:21][CH2:20][CH:19]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:18][CH2:17]2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH3:28][S:29]([OH:32])(=[O:31])=[O:30]>C(OCC)C>[CH3:28][S:29]([OH:32])(=[O:31])=[O:30].[F:12][C:9]([F:10])([F:11])[C:7]1[CH:6]=[C:5]([C:13]#[C:14][CH2:15][N:16]2[CH2:17][CH2:18][CH:19]([C:22]([CH3:23])([CH3:24])[CH3:25])[CH2:20][CH2:21]2)[CH:4]=[C:3]([C:2]([F:26])([F:27])[F:1])[CH:8]=1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 133730Flupropadine

Product 1

HCID 205264891-(3,5-Bistrifluoromethylphenyl)-3-(4-tert-butylpiperidino)prop-1-yne methanesulphonateYield 95.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 1-(3,5-bistrifluoromethylphenyl)-3-(4-tert-butylpiperidino)prop-1-yne (9.78 g) in anhydrous diethyl ether (12.5 ml) was treated with a solution of methanesulphonic acid (2.40 g) in anhydrous diethyl ether (12.5 ml), stirred and cooled. The solid precipitate was removed by filtration, washed with cold anhydrous diethyl ether and dried at 0.05 mm Hg for 2 hours, to give 1-(3,5-bistrifluoromethylphenyl)-3-(4-tert-butylpiperidino)prop-1-yne methanesulphonate (11.61 g), m.p. 164°-165° C., in the form of a white powder which had the elementary analysis C: 51.3%; H: 5.49%; N: 2.60% (C21H27F6NO3S requires C: 51.73%; H: 5.58%; N: 2.87%).

Workup

  1. temperaturecooled
  2. customThe solid precipitate was removed by filtration
  3. washwashed with cold anhydrous diethyl ether
  4. customdried at 0.05 mm Hg for 2 hours

Sources & evidence

ORD record
ord-78f022cad8e2421c9adf8015ee096779
Source dataset
uspto-grants-1982_08
Patent number
US04347252

Reaction notes

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