[OH-].[K+].[OH:3][C:4]1[C:12]2[O:11][C:10]([CH3:14])([CH3:13])[CH:9]([N:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)[C:8]=2[CH:7]=[CH:6][CH:5]=1.[Br:21][CH2:22][CH2:23][CH2:24][CH2:25]Br>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CCOCC>[Br:21][CH2:22][CH2:23][CH2:24][CH2:25][O:3][C:4]1[C:12]2[O:11][C:10]([CH3:13])([CH3:14])[CH:9]([N:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)[C:8]=2[CH:7]=[CH:6][CH:5]=1Crushed potassium hydroxide (19.6 g) and tetrabutyl ammonium chloride (1.7 g) are added to a solution of 7-hydroxy-3-piperidino-2,2-dimethylbenzofuran (14.4 g) in 1,4-dibromobutane (69.4 ml) and the mixture stirred at RT under nitrogen for 5 hours. The reaction mixture is diluted with ether, washed with water, extracted with 5% aq. HCl and the acidic phase washed with ether. The acidic phase is made basic thereby forming an oil which is taken up in ether, washed with sat'd aq. NaCl, dried, filtered and evaporated in vacuo affording the desired product as a liquid.
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