Sodium Hydroxide → 2-[2-(4-benzyl-1-piperazinyl)ethyl]-1-methyl-1H-naphth[1,2-d]imidazole
Reaction equation
Br[C:2]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:5]2[N:6]([CH3:24])[C:7]([CH2:9][CH2:10][N:11]3[CH2:16][CH2:15][N:14]([CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH2:13][CH2:12]3)=[N:8][C:4]=2[CH:3]=1.[OH-].[Na+]>C1(C)C=CC=CC=1>[CH2:17]([N:14]1[CH2:15][CH2:16][N:11]([CH2:10][CH2:9][C:7]2[N:6]([CH3:24])[C:5]3[C:25]4[C:30]([CH:2]=[CH:3][C:4]=3[N:8]=2)=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH2:12][CH2:13]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1Participants
4
Procedure
3.9 cc of toluene containing 2.62 g (0.013 mole) of (CH3OCH2CH2O)2NaAlH2 is added to a solution of 4.13 g (0.0089 mole) of the compound of Example 16 in 80 cc of toluene and the obtained mixture is refluxed with stirring under argon atmosphere. After 6 hours, when the reaction, which is followed by thin layer chromatography, is completed, 100 cc of 5% NaOH is added to the mixture and the toluene phase is separated and washed with a saturated NaCl solution. Upon evaporating the solvent, a crude product is obtained which is recrystallized from ethyl acetate:hexane 1:1, yielding 2 g of the compound of the title. M.p. 144°-46° C.
Workup
- temperaturethe obtained mixture is refluxed
- customwhen the reaction, which
- customthe toluene phase is separated
- washwashed with a saturated NaCl solution
- customUpon evaporating the solvent
- customa crude product is obtained which
- customis recrystallized from ethyl acetate:hexane 1:1
Sources & evidence
- ORD record
- ord-f8cb66d3303c423b8ce410b382419f62
- Source dataset
- uspto-grants-1982_11
- Patent number
- US04360674
Reaction notes
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