US 11,780,818 B2
Methods of making delmopinol and salts thereof
Venkataramana Reddy Yemireddy, Hyderabad (IN); Balraju Vadla, Hyderabad (IN); Vijaya Kumar Kongara, Hyderabad (IN); and Vidya Sagar Gottam, Hyderabad (IN)
Assigned to You First Services, Inc., Buffalo, NY (US)
Appl. No. 17/759,850
Filed by You First Services, Inc., Buffalo, NY (US)
PCT Filed Feb. 1, 2021, PCT No. PCT/US2021/016040
§ 371(c)(1), (2) Date Jul. 29, 2022,
PCT Pub. No. WO2021/155350, PCT Pub. Date Aug. 5, 2021.
Claims priority of provisional application 62/968,730, filed on Jan. 31, 2020.
Prior Publication US 2023/0094524 A1, Mar. 30, 2023
Int. Cl. C07D 265/30 (2006.01)
CPC C07D 265/30 (2013.01) 20 Claims
 
1. A method of making a delmopinol salt, comprising:
contacting

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with a first reaction mixture comprising:
morpholine,
a first solvent,
H2O2, and
Na2WO4.2H2O,
wherein

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is formed and X is an alcohol or protected alcohol;
contacting the

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with a second reaction mixture comprising:
p-toluenesulfonic acid,
a second solvent,
H2 gas at a pressure of at least 10 kg/cm2, and
Pd/C,
wherein

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is formed;
contacting the

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with a third reaction mixture comprising:
a third solvent,
a salt,
a halogenated ethyl alcohol, ethylene oxide, or a halogenated ethane having a protected alcohol, and
optionally, a base,
wherein

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is formed and X′ is an alcohol, protected alcohol, or halogen, and
contacting the

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with a metal salt,
wherein

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is formed and M+ is a metal cation,
with the proviso that the method does not comprise formation of

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