Aluminum(III) Chloride → 1'-Benzyl-6-chloro-3,4-dihydrospiro[chromene-2,4'-piperidine]
Reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[CH2:5]([N:12]1[CH2:17][CH2:16][C:15]2([CH2:26][C:25](=O)[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([Cl:28])[CH:23]=3)[O:18]2)[CH2:14][CH2:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>ClCCl>[CH2:5]([N:12]1[CH2:17][CH2:16][C:15]2([CH2:26][CH2:25][C:24]3[C:19](=[CH:20][CH:21]=[C:22]([Cl:28])[CH:23]=3)[O:18]2)[CH2:14][CH2:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1Participants
Procedure
To a stirred suspension of AlCl3 (3.04 g, 22.8 mmol) in dichloromethane (75 ml) tert-butylamine-borane (1:1) (3.98 g, 45.8 mmol) was added at 0° C., and the stirring was continued for 15 min at this temperature to obtain a clear solution. A solution of 1′-benzyl-6-chlorospiro[chromene-2,4′-piperidin]-4(3H)-one (2.61 g, 7.6 mmol) in dichloromethane (15 ml) was added dropwise. The stirring was continued for 2 h at 0° C. and for 3 h at room temperature. The reaction mixture was quenched by dropwise addition of 0.1 N aq. HCl. After the gas evolution has ceased, the layers were separated. The organic layer was washed with 0.1 N HCl (2×50 ml) and brine (50 ml), and dried over Na2SO4. The solvent was removed in vacuo to afford subtitle compound as colourless solid (1.63 g, 65%).
Workup
- additionwas added at 0° C.
- customto obtain a clear solution
- waitThe stirring was continued for 2 h at 0° C. and for 3 h at room temperature
- customThe reaction mixture was quenched by dropwise addition of 0.1 N aq. HCl
- customthe layers were separated
- washThe organic layer was washed with 0.1 N HCl (2×50 ml) and brine (50 ml)
- dry with materialdried over Na2SO4
- customThe solvent was removed in vacuo
Sources & evidence
- ORD record
- ord-b55a5ac9468c4b5695c09e32add1c227
- Source dataset
- uspto-grants-2008_11
- Patent number
- US07449475B2
Reaction notes
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