Sulfuric Acid → 1-(3,5-Bistrifluoromethylphenyl)-3-(4-tert-butylpiperidino)prop-1-yne hydrogensulphate

HRID 67928Notes

Reaction equation

HRID 67928 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.[S:28](=[O:32])(=[O:31])([OH:30])[OH:29]>C(OCC)C>[S:28]([OH:32])([OH:31])(=[O:30])=[O:29].[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 1118Sulfuric AcidHCID 133730Flupropadine

Product 1

HCID 867385581-(3,5-Bistrifluoromethylphenyl)-3-(4-tert-butylpiperidino)prop-1-yne hydrogensulphate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A stirred solution of 1-(3,5-bistrifluoromethylphenyl)-3-(4-tert-butylpiperidino)prop-1-yne (0.98 g) in anhydrous diethyl ether (50 ml) was treated with a solution of sulphuric acid (e.g. 1.84) in anhydrous diethyl ether (0.25 molar solution; 10 ml). The mixture was allowed to stand for 30 minutes and then filtered. The solid residue was washed with anhydrous diethyl ether (2×20 ml) and dried over phosphorus pentoxide at a pressure of 0.01 mg Hg for 48 hours, to give 1-(3,5-bistrifluoromethylphenyl)-3-(4-tert-butylpiperidino)prop-1-yne hydrogensulphate (1.15 g), m.p. 221°-222° C. in the form of a white powder which had the elementary analysis C: 49.1%; H: 5.02%; N: 2.76% (C20H25F6NO4S requires C: 49.07%; H: 5.15%; N: 2.86%).

Workup

  1. filtrationfiltered
  2. washThe solid residue was washed with anhydrous diethyl ether (2×20 ml)
  3. dry with materialdried over phosphorus pentoxide at a pressure of 0.01 mg Hg for 48 hours

Sources & evidence

ORD record
ord-985a842879254bc6be6e130eaec6c084
Source dataset
uspto-grants-1982_08
Patent number
US04347252

Reaction notes

Loading…