Methanol → 4-[4-[4-(4-Pyridyl)piperazin-1-yl]phenoxy]butyric acid, hydrochloride salt

HRID 266761Notes

Reaction equation

HRID 266761 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][N:10]([C:13]3[CH:25]=[CH:24][C:16]([O:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])=[CH:15][CH:14]=3)[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.CO.[ClH:28].N1C=CC=CC=1>C(OCC)(=O)C>[ClH:28].[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:8][CH2:9][N:10]([C:13]3[CH:14]=[CH:15][C:16]([O:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])=[CH:24][CH:25]=3)[CH2:11][CH2:12]2)=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 10176127Pyridinium chlorideHCID 189185114-[4-[4-(4-Pyridyl)piperazin-1-yl]phenoxy]butyric acid

Product 1

HCID 1317196124-[4-[4-(4-Pyridyl)piperazin-1-yl]phenoxy]butyric acid, hydrochloride saltYield 81.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of the product from Example 26 (1.5 g) and methanol (80 ml) was heated to reflux with stirring, and solid pyridine hydrochloride (0.5 g) was added. Heating was stopped and ethyl acetate (10 ml) was added. The reaction mixture was evaporated until a slight turbidity was observed. On further cooling, a precipitate formed which was collected, washed with ethyl acetate and dried to give the title compound (1.33 g) as a beige solid: m.p. 240° C. (dec); NMR (d6 -DMSO) δ 1.90 (2H, m), 2.36 (2H, t), 3.17 (4H, m), 3.83 (4H, m), 3.91 (2H, t), 6.89 (4H, q), 7.26 (2H, d), 8.25 (2H, d), 12.1 (1H, br), 13.75 (1H, br); m/Z 342 (H+H)+ ; calculated for C19H23N3O3. 1.0 HCl: C, 60.4%; H, 6.4%; N, 11.1%; found: C, 60.0%; H, 6.4%, N, 10.8%.

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. temperatureHeating
  4. customThe reaction mixture was evaporated until a slight turbidity
  5. customOn further cooling, a precipitate formed which
  6. customwas collected
  7. washwashed with ethyl acetate
  8. customdried

Sources & evidence

ORD record
ord-a7b99d9295484de688cae970bad00e48
Source dataset
uspto-grants-1997_07
Patent number
US05652242

Reaction notes

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