Methanol → HCID 23453810, compound
Reaction equation
C1(C2C=CC=CC=2)C=CC=CC=1NC#CCC.[CH2:18]([NH:23][CH2:24][C:25]#[C:26][CH:27]([OH:40])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH2:19][CH:20]([CH3:22])[CH3:21].CO>[Pd].[Pt].C(O)C>[CH2:18]([NH:23][CH2:24][CH2:25][CH2:26][CH:27]([OH:40])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH2:19][CH:20]([CH3:21])[CH3:22]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Procedure
The biphenylyl alkynylamine next is reduced to yield the corresponding biphenylyl alkylamine of the invention. Such exhaustive reduction typically is carried out by hydrogenation in the presence of a catalyst such as palladium or platinum. For example, a biphenylyl butynylamine such as N-isopentyl-4-hydroxy-4-(1,1'-biphenyl-2-yl)-2-butynylamine is dissolved in a suitable organic solvent such as methanol or ethanol and stirred for about two to four hours at about 20 to about 50° C. under a hydrogen atmosphere of about 20 to about 80 psi, in the presence of a hydrogenation catalyst such as palladium suspended on carbon. The reduced product, for instance N-isopentyl-4-hydroxy-4-(1,1'-biphenyl-2-yl)butylamine, is isolated by filtering the reaction mixture to remove the catalyst and then evaporating the reaction solvent from the filtrate. The amine thus formed can be further purified if desired by standard methods such as acid and base extraction, crystallization from solvents such as diethyl ether or Skelly-B, salt formation, chromatography and the like.
Sources & evidence
- ORD record
- ord-faf090d50b3049bda2c5e970fa735986
- Source dataset
- uspto-grants-1981_07
- Patent number
- US04277471
Reaction notes
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