Reaction equation
[NH2:1][CH2:2][C:3]#[C:4][CH2:5][N:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][CH3:19])[CH2:8][CH2:7]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[NH2:1][CH2:2]/[CH:3]=[CH:4]/[CH2:5][N:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][CH3:19])[CH2:8][CH2:7]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 1-amino-4-[4-(2-methoxyphenyl)-1-piperazinyl]-2-butyne (13.4 g) in tetrahydrofuran (150 ml) was added dropwise over 45 mins to a suspension of lithium aluminum hydride (3.91 g) in tetrahydrofuran (500 ml), while the reaction temperature was maintained below 5° C. The reaction mixture was allowed to warm to room temperature and was stirred at room temperature for 20 hrs. Water (3.9 ml), 15% aqueous sodium hydroxide (3.9 ml) and water (12 ml) were added sequentially, while the reaction temperature was kept below 30° C. The precipitate was filtered through a bed of celite, washed three times with diethyl ether (100 ml), filtered, and the filtrate was concentrated. Recrystallization of the residue from hexane gave 7.31 g (54%) of product, mp 63°-67° C.
Workup
- temperaturewas maintained below 5° C
- customwas kept below 30° C
- filtrationThe precipitate was filtered through a bed of celite
- washwashed three times with diethyl ether (100 ml)
- filtrationfiltered
- concentrationthe filtrate was concentrated
- customRecrystallization of the residue from hexane
Sources & evidence
- ORD record
- ord-90c1e06b62c14a2092b38bcda47dd4ff
- Source dataset
- uspto-grants-1993_03
- Patent number
- US05194436
Linked notes
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