Potassium Iodide → cis-N-[1-[3-(4-fluorophenoxy)propyl]-3-hydroxy-4-piperidinyl]benzamide

HRID 1088393Notes

Reaction equation

HRID 1088393 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1.[OH:13][C@H:14]1[C@@H:19]([NH:20][C:21](=[O:28])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:18][CH2:17][NH:16][CH2:15]1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>CC(C)CC(=O)C>[F:12][C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH2:3][CH2:2][N:16]2[CH2:17][CH2:18][C@H:19]([NH:20][C:21](=[O:28])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C@H:14]([OH:13])[CH2:15]2)=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 743911-(3-Chloropropoxy)-4-fluorobenzeneHCID 15096814cis-N-(3-hydroxy-4-piperidinyl)benzamide

Product 1

HCID 15096855cis-N-[1-[3-(4-fluorophenoxy)propyl]-3-hydroxy-4-piperidinyl]benzamideYield 57%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 4.1 parts of 1-(3-chloropropoxy)-4-fluorobenzene, 4.4 parts of cis-N-(3-hydroxy-4-piperidinyl)-benzamide, 3.8 parts of sodium carbonate, 0.1 parts of potassium iodide and 160 parts of 4-methyl-2-pentanone was stirred and refluxed for 20 hours. The reaction mixture was cooled to room temperature and washed with water. The organic phase was dried, filtered and evaporated. The residue was crystallized from 2-propanol, yielding 4.2 parts (57%) of cis-N-[1-[3-(4-fluorophenoxy)propyl]-3-hydroxy-4-piperidinyl]benzamide; mp. 130.5° C. (compound 72).

Workup

  1. temperaturerefluxed for 20 hours
  2. washwashed with water
  3. customThe organic phase was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was crystallized from 2-propanol

Sources & evidence

ORD record
ord-f00cc97de3d042dd8baac7287003f6fa
Source dataset
uspto-grants-1990_10
Patent number
US04962115

Reaction notes

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