1,4-Dibromobutane → 7-(4-Bromobutoxy)-3-piperidino-2,2-dimethylbenzofuran

HRID 65014

Reaction equation

HRID 65014 reaction equation
[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]=1

Participants

6

Reactant 3

HCID 80561,4-DibromobutaneHCID 14797Potassium HydroxideHCID 141266507-Hydroxy-3-piperidino-2,2-dimethylbenzofuran

Product 1

HCID 212890017-(4-Bromobutoxy)-3-piperidino-2,2-dimethylbenzofuran

Reagents, catalysts & solvents 2

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

Crushed 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.

Workup

  1. washwashed with water
  2. extractionextracted with 5% aq. HCl
  3. washthe acidic phase washed with ether
  4. customThe acidic phase is made basic thereby forming an oil which
  5. washwashed with sat'd aq. NaCl
  6. customdried
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-931ac3f574254115bad1dfd8de4e47f9
Source dataset
uspto-grants-1986_09
Patent number
US04612309

Linked notes

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