Benzene, (3-bromopropoxy)- → HCID 23036406, compound

HRID 1709874Notes

Reaction equation

HRID 1709874 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[OH:9])=[CH:4][CH:3]=1.Br[CH2:24][CH2:25][CH2:26][O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[C:34](=[O:37])([OH:36])[O-].[Na+]>C(O)CCC>[OH2:9].[C:8]([OH:9])(=[O:27])[C:34]([OH:36])=[O:37].[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:16]2[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=2)([CH:10]2[CH2:11][CH2:12][N:13]([CH2:24][CH2:25][CH2:26][O:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:14][CH2:15]2)[OH:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 68522Benzene, (3-bromopropoxy)-HCID 516892Sodium BicarbonateHCID 11208889Bis(4-fluorophenyl)(piperidin-4-yl)methanol

Product 1

HCID 23036406HCID 23036406, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 3.37 g (0.011 mole) of α,α-bis(p-fluorophenyl)-4-piperidinemethanol, 2.52 g (0.011 mole) of (3-bromopropoxy)benzene and sodium bicarbonate (3.7 g, 0.035 mole) in 200 ml of 1-butanol was heated overnight at reflux. The butanol was removed by the rotary evaporator, and the residue partitioned between chloroform and water. Removal of the chloroform in vacuo gave a dark brown oil, the free base of the title compound. The base was converted to the oxalate salt and recrystallized from methanol-ethyl ether to give 1.41 (23.9%) of white solid, m.p. 163° C.

Workup

  1. temperaturewas heated overnight
  2. temperatureat reflux
  3. customThe butanol was removed by the rotary evaporator
  4. customthe residue partitioned between chloroform and water
  5. customRemoval of the chloroform in vacuo
  6. customgave a dark brown oil

Sources & evidence

ORD record
ord-068dd547ed754360909651ee497c9263
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

Loading…