Tetrahydrofuran → HCID 86711158, compound
Reaction equation
[CH3:1][C:2]1[N:12]=[C:11]2[N:6]([CH2:7][CH2:8][CH2:9][CH:10]2[OH:13])[C:4](=[O:5])[C:3]=1[CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][CH:19]([C:22]2[C:23]3[CH:24]=[CH:25][C:26]([F:31])=[CH:27][C:28]=3[O:29][N:30]=2)[CH2:18][CH2:17]1.[C:32]([NH:39][CH2:40][CH2:41][CH2:42]Br)([O:34]C(C)(C)C)=O.[CH2:44]1OCCOCCOCCOCCOCCOC1.[H-].[Na+].[CH2:64]1[CH2:68]OC[CH2:65]1>>[F:31][C:26]1[CH:25]=[CH:24][C:23]2[C:22]([CH:19]3[CH2:20][CH2:21][N:16]([CH2:15][CH2:14][C:3]4[C:4](=[O:5])[N:6]5[CH2:7][CH2:8][CH2:9][CH:10]([O:13][CH2:42][CH2:41][CH2:40][NH:39][C:32](=[O:34])[C:64]([CH3:65])([CH3:68])[CH3:44])[C:11]5=[N:12][C:2]=4[CH3:1])[CH2:17][CH2:18]3)=[N:30][O:29][C:28]=2[CH:27]=1Participants
6
Procedure
A solution of paliperidone (746.26 mg, 1.75 mmol) in THF (15 mL) was treated with 3-(Boc-amino)propyl bromide (500 mg, 2.10 mmol), 18-Crown-6 (231.25 mg, 0.874 mmol) and sodium hydride (60 w/w %, 139.97 mg, 3.5 mmol). The mixture was stirred at room temperature for 6 h. The solvent was removed under vacuum, dissolved in dichloromethane/water (50 mL/50 mL) and the aqueous layer extracted with dichloromethane (three times 50 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated to give the title compound, which was used without further purification in the next step.
Workup
- customThe solvent was removed under vacuum
- dissolutiondissolved in dichloromethane/water (50 mL/50 mL)
- extractionthe aqueous layer extracted with dichloromethane (three times 50 mL)
- dry with materialThe combined organic layers were dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-e2f11cf047ed4b0fa7ee6929aeed0f64
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09394354B2
Reaction notes
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