Water → 7-(3-Bromopropoxy)-3-piperidino-2,2-dimethylbenzofuran

HRID 3775

Reaction equation

HRID 3775 reaction equation
[OH-].[K+].O.[OH:4][C:5]1[C:13]2[O:12][C:11]([CH3:15])([CH3:14])[CH:10]([N:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)[C:9]=2[CH:8]=[CH:7][CH:6]=1.[Br:22][CH2:23][CH2:24][CH2:25]Br>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)C>[Br:22][CH2:23][CH2:24][CH2:25][O:4][C:5]1[C:13]2[O:12][C:11]([CH3:14])([CH3:15])[CH:10]([N:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)[C:9]=2[CH:8]=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 962WaterHCID 80011,3-DibromopropaneHCID 14797Potassium HydroxideHCID 141266507-Hydroxy-3-piperidino-2,2-dimethylbenzofuran

Product 1

HCID 141266517-(3-Bromopropoxy)-3-piperidino-2,2-dimethylbenzofuran

Reagents, catalysts & solvents 2

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

Potassium hydroxide (1.47 g), tetrabutyl ammonium chloride (0.77 g) and H2O (1 ml) are added to a solution of the product obtained in Step 6. (6.6 g) in 1,3-dibromopropane (27 ml). The reaction mixture is stirred for 20 hours and diluted with diethyl ether and washed with 5% aq. HCl. The acidic solution is washed with ether and basified, affording an oil which is taken up in ether, washed with sat'd NaCl, dried, filtered and evaporated in vacuo affording the desired product as an oil.

Workup

  1. washwashed with 5% aq. HCl
  2. washThe acidic solution is washed with ether
  3. custombasified, affording an oil which
  4. washwashed with sat'd NaCl
  5. customdried
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-f0acfd39ea7a462683b5b3c43269d05e
Source dataset
uspto-grants-1988_02
Patent number
US04722925

Linked notes

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