Sodium Hydroxide → HCID 20068661, compound

HRID 981993Notes

Reaction equation

HRID 981993 reaction equation
[F:1][C:2]1[CH:30]=[CH:29][C:5]([C:6]([CH:8]([CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][N:19]([C:22]3[N:27]=[CH:26][C:25]([F:28])=[CH:24][N:23]=3)[CH2:18][CH2:17]2)C(OCC)=O)=O)=[CH:4][CH:3]=1.[OH-:31].[Na+].C([O-])(O)=O.[Na+]>Cl>[F:1][C:2]1[C:3]2[C:4](=[CH:30][CH:2]=[CH:3][CH:4]=2)[C:5]([CH2:6][C:8](=[O:31])[CH2:14][CH2:15][N:16]2[CH2:17][CH2:18][N:19]([C:22]3[N:23]=[CH:24][C:25]([F:28])=[CH:26][N:27]=3)[CH2:20][CH2:21]2)=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 20068653HCID 20068653, compound

Product 1

HCID 20068661HCID 20068661, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
23 °C

Procedure

A mixture of Ethyl 2-(4-fluorobenzoyl)-4-(4-(5-fluoro-2-pyrimidinyl)piperazin-1-yl)butanoate (2.95 g, 6.3 mmol) in aqueous HCl (65 mL, 1N) was refluxed for 2 h, cooled at 23° C. and basified, first with aqueous NaOH solution (30 mL, 2N) and then with saturated NaHCO3 solution until pH=9. The aqueous solution was extracted with CH2Cl2 (3×150 mL). Organic extracts were combined, washed with water (30 mL) and brine, dried (MgSO4) and concentrated to dryness. The crude material was chromatographed on silica gel using a mixture of 50% CH2Cl2 in EtOAc. Appropriate fractions were combined and solvent evaporated under reduced pressure leaving 2.3 g (92%), mp 119°-120° C. Recrystallization from EtOH afforded analytical sample; mp 120°-1° C.; 1H NMR (CDCl3, 200 MHz) δ: 2.03 (t, J=7.0 Hz, CH2CH2CH2, 2H), 2.4-2.6 (m, 6H), 3H (t, J=7.0, CH2CO, 2H), 3.8-3.9 (m, 4H), 7.1-7.2 (m, 1H), 7.5-7.8 (m, 2H), 7.9-8.0 m, 1H), 8.18 (s), 8.1-8.3 (m, 3H), 8.7-8.8 (m, 1H); IR (KBr) ν: 1681, 1630, 1611, 1600, 1575, 1555, 1494 cm-1 ; UV (CH3CN) λ: 226 (ε 40377), 298 (ε 7498);

Workup

  1. temperaturewas refluxed for 2 h
  2. extractionThe aqueous solution was extracted with CH2Cl2 (3×150 mL)
  3. washwashed with water (30 mL) and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated to dryness
  6. customThe crude material was chromatographed on silica gel using
  7. additiona mixture of 50% CH2Cl2 in EtOAc
  8. customsolvent evaporated under reduced pressure
  9. customleaving 2.3 g (92%), mp 119°-120° C
  10. customRecrystallization from EtOH afforded analytical sample

Sources & evidence

ORD record
ord-62dcbcb50e804bb18d50d4296bfd9e4b
Source dataset
uspto-grants-1991_02
Patent number
US04994460

Reaction notes

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