1,8-Diazabicyclo(5.4.0)undec-7-ene → 5-Chloro-6-(piperidin-1-yl)-2,3-dihydrobenzofuran

HRID 637668Notes

Reaction equation

HRID 637668 reaction equation
N12CCCN=C1CCCCC2.Br[CH2:13][CH2:14][C:15]1[CH:20]=[C:19]([Cl:21])[C:18]([N:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[CH:17][C:16]=1[OH:28]>C(Cl)Cl>[Cl:21][C:19]1[C:18]([N:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[CH:17][C:16]2[O:28][CH2:13][CH2:14][C:15]=2[CH:20]=1

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 202556591-Bromo-2-[5-chloro-2-hydroxy-4-(piperidin-1-yl)-phenyl]-ethane

Product 1

HCID 202556365-Chloro-6-(piperidin-1-yl)-2,3-dihydrobenzofuran

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.2 ml (8.0 mmole) of 1,8-diazabicyclo[5.4.0]-undec-7-ene (DBU) are added at 0° to a solution of 2.50 g (7.8 mmole) of 1-bromo-2-[5-chloro-2-hydroxy-4-(piperidin-1-yl)-phenyl]-ethane in 50 ml of absolute methylene chloride and the whole is then stirred for 3 hours at room temperature. The reaction mixture is washed with saturated sodium chloride solution and the organic phases are combined, dried over sodium sulphate and concentrated in a vacuum rotary evaporator. The residue is chromatographed over silica gel using methylene chloride as eluant. Recrystallisation from petroleum ether yields 5-chloro-6-(piperidin-1-yl)-2,3-dihydrobenzofuran having a melting point of 38°-40°.

Workup

  1. washThe reaction mixture is washed with saturated sodium chloride solution
  2. dry with materialdried over sodium sulphate
  3. concentrationconcentrated in a vacuum rotary evaporator
  4. customThe residue is chromatographed over silica gel
  5. customRecrystallisation from petroleum ether

Sources & evidence

ORD record
ord-2b1bd3379f4243f2b97f8d975a5221ae
Source dataset
uspto-grants-1985_12
Patent number
US04558043

Reaction notes

Loading…