Hydrochloric Acid → HCID 53733203, compound

HRID 1180189Notes

Reaction equation

HRID 1180189 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:16]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][CH:27]4[CH2:32][CH2:31][CH2:30][CH2:29][NH:28]4)=[CH:20][CH:19]=3)[C:15]3[C:10](=[CH:11][C:12]([O:33][CH3:34])=[CH:13][CH:14]=3)[C:9]2=O)=[CH:4][CH:3]=1.Cl.C(=O)(O)[O-].[Na+]>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:9][C:10]3[C:15](=[CH:14][CH:13]=[C:12]([O:33][CH3:34])[CH:11]=3)[CH:16]2[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][NH:28]3)=[CH:20][CH:19]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 57038062HCID 57038062, compound

Product 1

HCID 53733203HCID 53733203, compoundYield 61.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-(4-fluorophenyl)-6-methoxy-3-{4-[(2-piperidyl)ethoxy]benzyl}isoindolin-1-one (0.50 g, 1.05 mmol) in tetrahydrofuran (10 mL) under nitrogen was added a 1.5 M solution of borane-tetrahydrofuran complex in tetrahydrofuran (2 mL, 3 mmol). After heating at reflux for 5 hours, the reaction was cooled to room temperature, 6 N HCl solution (6 mL) was added, and the reaction was stirred for 1 hour at room temperature. The mixture was basified with a saturated sodium bicarbonate solution and extracted with CH2Cl2. The organic layer was dried over MgSO4, filtered, and concentrated. The residue was then purified by chromatography (SiO2, 20-30% ethyl acetate/hexane) to provide the title compound (0.297 g, 61% yield): 1H NMR (CDCl3) 7.05 (t, 2H), 6.91 (d, 1H), 6.78 (dd, 1H), 6.61-6.72 (m, 7H), 5.24 (m, 1H), 4.30-4.41 (m, 3H), 4.15 (dd, 1H), 3.80 (s, 3H), 3.17 (t, 2H), 2.98-3.10 (m, 4H), 2.91 (m, 2H), 1.81 (m, 4H), 1.56 (m, 2H); ES-MS (m/z) 461 [M+H]+.

Workup

  1. temperatureAfter heating
  2. temperatureat reflux for 5 hours
  3. extractionextracted with CH2Cl2
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was then purified by chromatography (SiO2, 20-30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-194de36817d8459aabf078fd6e526a11
Source dataset
uspto-grants-2007_10
Patent number
US07279489B2

Reaction notes

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