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

HRID 3776
Notes
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Reaction equation

HRID 3776 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 ChlorideCatalyst
HCID 3283
Diethyl Ether
Solvent
2×

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-e1cc7aae472c4f0e89601c6881976e37
Source dataset
uspto-grants-1988_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04722925

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes