Reaction #81526

ord-a175068cb1484a3e8e9a7acf931dcddd

Reaction equation

Cc1noc(-c2ccccc2N(C)C(=O)OC2CCN(CCNCS(C)(=O)=O)CC2)n1

[1-[2-[(Methylsulphonyl)methylamino]ethyl]-4-piperidinyl]methyl[2-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]carbamate

$O=C(O)/C=C\C(=O)O$

maleic acid

→

$Cc1noc(-c2ccccc2N(C)C(=O)OC2CCN(CCNCS(C)(=O)=O)CC2)n1.O=C(O)/C=C\C(=O)O$

title compound

Yield 73.8%

$Cc1noc(-c2ccccc2N(C)C(=O)OC2CCN(CCNCS(C)(=O)=O)CC2)n1.O=C(O)/C=C\C(=O)O$

[1-[2-[(Methylsulphonyl)methylamino]ethyl]4-piperidinyl]methyl[2-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]carbamate (Z)-2-butenedioate

Yield 73.8%

Reactants

[1-[2-[(Methylsulphonyl)methylamino]ethyl]-4-piperidinyl]methyl[2-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]carbamate

$O=C(O)/C=C\C(=O)O$

maleic acid

Reagents

None

Solvents

ethyl acetate

Conditions

Detailed conditions

See reaction.notes.procedure_details.

Workup

1
workup.ADDITIONadded
2
OtherWhite crystals precipitated
3
FiltrationThese were filtered
4
Otherdried under vacuum

Procedure

[1-[2-[(Methylsulphonyl)methylamino]ethyl]-4-piperidinyl]methyl[2-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]carbamate (55 mg) was dissolved in boiling ethyl acetate (1 ml) and maleic acid (17 mg) in hot ethyl acetate (1 ml) added. White crystals precipitated. These were filtered and dried under vacuum to give the title compound (51 mg), as a white powder, m.p. 170°-172°

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05618827uspto-grants-1997_04