Methanesulfonic Acid → Methanesulfonate

HRID 66163Notes

Reaction equation

HRID 66163 reaction equation
C(O[C:4]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[CH:5][C:6]1[CH2:10][CH2:9][CH2:8][N:7]=1)C.F[B-](F)(F)F.[CH3:22][S:23]([OH:26])(=[O:25])=[O:24].[NH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1>C(O)(C)C>[N:27]1([C:4]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[CH:5][C:6]2[CH2:10][CH2:9][CH2:8][N:7]=2)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1.[CH3:22][S:23]([O-:26])(=[O:25])=[O:24]

Participants

6

Reactant 3

HCID 6395Methanesulfonic AcidHCID 8082PiperidineHCID 867362142-(2-Ethoxy-2-phenyl-ethenyl)-1-pyrroline tetrafluoroborate

Product 2

HCID 85257MethanesulfonateHCID 536780182-(1-Piperidyl-2-phenylethenyl]-1-pyrroline-

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Crude 2-[2-(1-piperidyl)-2-phenyl-ethenyl]-1-pyrroline is produced by refluxing for 12 hours the solution of 9.1 g (0.03 mole) of 2-(2-ethoxy-2-phenyl-ethenyl)-1-pyrroline-tetrafluoroborate in 25 ml of piperidine, and processing the reaction mixture analogously to Example 1. By the addition of 2.8 g of methanesulphonic acid to the solution of the crude base in isopropanol, concentration of this solution in the rotary evaporator and recrystallisation of the residue from acetone/hexane, there is obtained 2-[2-(1-piperidyl-2-phenylethenyl]-1-pyrroline-(1:1)-methanesulphonate, m.p. 123°-124°.

Workup

  1. customin the rotary evaporator and recrystallisation of the residue from acetone/hexane

Sources & evidence

ORD record
ord-aecd6f8d4454451f8f5e03adc516ea9d
Source dataset
uspto-grants-1978_12
Patent number
US04130652

Reaction notes

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