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

HRID 1193666Notes

Reaction equation

HRID 1193666 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 (0.92 g, 0.011 mole) in 200 ml of 1-butanol was heated overnight to 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-diethyl ether to give 1.41 g (23.9%) of white solid, m.p. 153° C.

Workup

  1. temperaturewas heated overnight
  2. temperatureto 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-d8740f4d690e4259a33309890413b7fd
Source dataset
uspto-grants-1989_03
Patent number
US04810713

Reaction notes

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