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

HRID 1290536Notes

Reaction equation

HRID 1290536 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 51 (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 (d6DMSO) 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), 1.21(1H,br), 13.75(1H,br); m/Z 342 (M+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-ad6f554440a74c59a0114cd8026c0009
Source dataset
uspto-grants-1998_05
Patent number
US05750754

Reaction notes

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