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

HRID 979479Notes

Reaction equation

HRID 979479 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-0a65f3be35134100bf8d1853a2353634
Source dataset
uspto-grants-1987_05
Patent number
US04668673

Reaction notes

Loading…