Hydrochloric Acid → 161178-07-0
Reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH2:12][CH:13]2[O:18][CH2:17][CH2:16][N:15](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH2:14]2)=[C:6]2[C:10]=1[CH2:9][CH2:8][CH2:7]2.Cl.C(=O)([O-])O.[Na+]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH2:12][CH:13]2[O:18][CH2:17][CH2:16][NH:15][CH2:14]2)=[C:6]2[C:10]=1[CH2:9][CH2:8][CH2:7]2Participants
Procedure
To 20 ml of a methanalic solution of 0.54 g of 2-[[(7-fluoro-4-indanyl)oxy]methyl]-4-tritylmorpholine was added a methanolic solution (5 ml) of concentrated hydrochloric acid (1.30 g, 12.8 mmol) at room temperature, followed by stirring for 30 minutes. After completion of the reaction, the reaction mixture was neutralized with a saturated aqueous solution of sodium hydrogencarbonate. The solvent was evaporated, and a saturated aqueous sodium chloride solution was added to the resulting residue, followed by extraction with chloroform. The extract was washed with a saturated aqueous sodium chloride solution and dried over magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography to obtain 2-[[(7-fluoro-4-indanyl)oxy]methyl]morpholine (0.236 g) as a colorless oily substance from the chloroform-methanol-concentrated ammonia (10:1:0.1) eluate.
Workup
- customAfter completion of the reaction
- customThe solvent was evaporated
- additiona saturated aqueous sodium chloride solution was added to the resulting residue
- extractionfollowed by extraction with chloroform
- washThe extract was washed with a saturated aqueous sodium chloride solution
- dry with materialdried over magnesium sulfate
- customThe solvent was evaporated
- customthe resulting residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-a438ef360f0143759bed36df008e77c9
- Source dataset
- uspto-grants-1996_05
- Patent number
- US05521180
Reaction notes
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