Oxalic Acid → [4-[3-[4-[Bis(4-fluorophenyl)hydroxymethyl]-1-piperidinyl]propoxy]phenyl]carbamic acid ethyl ester oxalate hydrate

HRID 1709899Notes

Reaction equation

HRID 1709899 reaction equation
C(O)(=O)C(O)=[O:3].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.[CH2:58]([O:60][C:61](=[O:74])[NH:62][C:63]1[CH:68]=[CH:67][C:66]([O:69][CH2:70][CH2:71][CH2:72]Cl)=[CH:65][CH:64]=1)[CH3:59].C(=O)([O-])[O-].[Na+].[Na+].[C:81]([OH:86])(=[O:85])[C:82]([OH:84])=[O:83]>CN(C)C=O.C(OCC)(=O)C.[I-].[K+]>[OH2:3].[C:81]([OH:86])(=[O:85])[C:82]([OH:84])=[O:83].[CH2:58]([O:60][C:61](=[O:74])[NH:62][C:63]1[CH:68]=[CH:67][C:66]([O:69][CH2:70][CH2:71][CH2:72][N:48]2[CH2:47][CH2:46][CH:45]([C:43]([C:51]3[CH:52]=[CH:53][C:54]([F:57])=[CH:55][CH:56]=3)([C:40]3[CH:41]=[CH:42][C:37]([F:36])=[CH:38][CH:39]=3)[OH:44])[CH2:50][CH2:49]2)=[CH:65][CH:64]=1)[CH3:59]

Participants

9

Reactant 5

HCID 971Oxalic AcidHCID 10340Sodium CarbonateHCID 11208889Bis(4-fluorophenyl)(piperidin-4-yl)methanolHCID 14407186N-[4-(3-Chloropropoxy)phenyl]carbamic acid ethyl esterHCID 230363354-(Diphenylmethylene)-1-(3-phenoxypropyl)piperidine oxalate

Product 1

HCID 70373334[4-[3-[4-[Bis(4-fluorophenyl)hydroxymethyl]-1-piperidinyl]propoxy]phenyl]carbamic acid ethyl ester oxalate hydrateYield 50%

Reagents, catalysts & solvents 3

HCID 4875Potassium IodideCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

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(4-fluorophenyl)-4-piperidinemethanol, 2.6 (0.01 mole) of N-[4-(3-chloropropoxy) phenyl]carbamic acid ethyl ester, 5.3 g (0.05 mole) of anhydrous sodium carbonate and 0.3 g of potassium iodide in 100 ml of dimethylformamide heated in a steambath for 24 hr gave a gum as residue. The gum was converted to the oxalic acid salt in ethyl acetate and the solid was recrystallized from 2-propanol to yield 32 g (50%) of title compound as a white solid, mp 70°-90° C.

Workup

  1. customThis compound was prepared
  2. temperatureheated in a steambath for 24 hr
  3. customgave a gum as residue
  4. customthe solid was recrystallized from 2-propanol

Sources & evidence

ORD record
ord-4915868faa5542e2bf68bd1952a72ade
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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