Sodium Carbonate → 4-[3-[4-[Bis(4-fluorophenyl)hydroxymethyl]-1-piperidinyl]propoxy]-3-methoxybenzeneacetic acid ethyl ester

HRID 1460258Notes

Reaction equation

HRID 1460258 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.[CH2:23]([O:25][C:26](=[O:41])[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH2:36][CH2:37]Cl)=[C:30]([O:39][CH3:40])[CH:29]=1)[CH3:24].C(=O)([O-])[O-].[Na+].[Na+].[K]>CN(C)C=O>[CH2:23]([O:25][C:26](=[O:41])[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH2:36][CH2:37][N:13]2[CH2:12][CH2:11][CH:10]([C:8]([C:16]3[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=3)([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[OH:9])[CH2:15][CH2:14]2)=[C:30]([O:39][CH3:40])[CH:29]=1)[CH3:24]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 5462222PotassiumHCID 11208889Bis(4-fluorophenyl)(piperidin-4-yl)methanolHCID 144071784-(3-Chloropropoxy)-3-methoxybenzeneacetic acid ethyl ester

Product 1

HCID 144071074-[3-[4-[Bis(4-fluorophenyl)hydroxymethyl]-1-piperidinyl]propoxy]-3-methoxybenzeneacetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 9.1 g (0.03 mole) of [α,α-bis(p-fluorophenyl)]-4-piperidinemethanol and 8.6 g (0.03 mole) of 4-(3-chloropropoxy)-3-methoxybenzeneacetic acid ethyl ester, 10.6 g (0.1 mole) of anhydrous sodium carbonate and 0.5 g of potassium iode in 150 ml of dimethylformamide was heated on a steambath for 20 hr. The mixture was concentrated under reduced pressure and the residue was partitioned between water and benzene. The benzene layer was washed with water and saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give an off-white solid which was recrystallized from isopropyl ether/2-propanol. The yield of the title compound was 12.7 g (77%), mp 110°-112° C.

Workup

  1. temperaturewas heated on a steambath for 20 hr
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customthe residue was partitioned between water and benzene
  4. washThe benzene layer was washed with water and saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto give an off-white solid which
  8. customwas recrystallized from isopropyl ether/2-propanol

Sources & evidence

ORD record
ord-c53917da31a547788d5556d74837e03e
Source dataset
uspto-grants-1991_12
Patent number
US05070087

Reaction notes

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