Hydrochloric Acid → 1-[4-[3-[4-[Bis(4-fluorophenyl)hydroxymethyl]-1-piperidinyl]propoxy]-2-methoxyphenyl]ethanone hydrochloride

HRID 1709893Notes

Reaction equation

HRID 1709893 reaction equation
C(O)(=O)C(O)=O.C1(C(C2C=CC=CC=2)=C2CCN(CCCOC3C=CC=CC=3)CC2)C=CC=CC=1.[F:36][C:37]1[CH:42]=[CH:41][C:40]([C:43]([C:51]2[CH:56]=[CH:55][C:54]([F:57])=[CH:53][CH:52]=2)([CH:45]2[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]2)[OH:44])=[CH:39][CH:38]=1.[Cl:58][CH2:59][CH2:60][CH2:61][O:62][C:63]1[CH:68]=[CH:67][C:66]([C:69](=[O:71])[CH3:70])=[C:65]([O:72][CH3:73])[CH:64]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+].Cl>C(O)CCC>[ClH:58].[F:36][C:37]1[CH:42]=[CH:41][C:40]([C:43]([C:51]2[CH:52]=[CH:53][C:54]([F:57])=[CH:55][CH:56]=2)([OH:44])[CH:45]2[CH2:46][CH2:47][N:48]([CH2:59][CH2:60][CH2:61][O:62][C:63]3[CH:68]=[CH:67][C:66]([C:69](=[O:71])[CH3:70])=[C:65]([O:72][CH3:73])[CH:64]=3)[CH2:49][CH2:50]2)=[CH:39][CH:38]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 11208889Bis(4-fluorophenyl)(piperidin-4-yl)methanolHCID 144071823-(p-Acetyl-m-methoxyphenoxy)propyl chlorideHCID 230363354-(Diphenylmethylene)-1-(3-phenoxypropyl)piperidine oxalate

Product 1

HCID 230364381-[4-[3-[4-[Bis(4-fluorophenyl)hydroxymethyl]-1-piperidinyl]propoxy]-2-methoxyphenyl]ethanone hydrochloride

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

This compound was prepared according to the procedure used to synthesize the compound of Example 1. A mixture of 3.0 g (0.01 mole) of [α,α-bis(p-fluorophenyl)]-4-piperidinemethanol, 2.4 g (0.01 mole) of 1-[4-(3-chloropropoxy)-2-methoxyphenyl]ethanone, 5.3 g (0.05 mole) of anhydrous sodium carbonate and 0.3 g of potassium iodide in 100 ml of 1-butanol gave a gum as residue. The gum was purified by column chromatography on 80 g of Florisil® and the fractions eluted with 20% acetone in benzene were combined and concentrated under reduced pressure to give a solid as residue. The solid was converted to the hydrochloride and this solid was recrystallized from 2-propanol-isopropyl ether to yield 2.2 g (40%) of white power, m.p. 196°-197° C.

Workup

  1. customThis compound was prepared
  2. customgave a gum as residue
  3. customThe gum was purified by column chromatography on 80 g of Florisil®
  4. washthe fractions eluted with 20% acetone in benzene
  5. concentrationconcentrated under reduced pressure
  6. customto give a solid as residue
  7. customthis solid was recrystallized from 2-propanol-isopropyl ether
  8. customto yield 2.2 g (40%) of white power, m.p. 196°-197° C.

Sources & evidence

ORD record
ord-1ac9691701d44ee6be7327f1ab30573e
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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