Water → Ammonium Hydroxide

HRID 2057061Notes

Reaction equation

HRID 2057061 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH:9][CH:10]2[CH2:15][CH2:14][CH:13]([OH:16])[CH2:12][CH2:11]2)[N:3]=1.[CH:17]1([NH2:24])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.[OH-].[Na+].O>CC(C)=O>[OH-:16].[NH4+:3].[Cl:8][C:6]1[N:7]=[C:2]([NH:24][CH:17]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[N:3]=[C:4]([NH:9][CH:10]2[CH2:15][CH2:14][CH:13]([OH:16])[CH2:12][CH2:11]2)[N:5]=1

Participants

7

Reactant 4

HCID 962WaterHCID 2899CycloheptylamineHCID 14798Sodium HydroxideHCID 59659976HCID 59659976, compound

Product 2

HCID 14923Ammonium HydroxideHCID 59659979HCID 59659979, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To 155a (1.0003 g, 3.8 mmol) dissolved in acetone (20 mL) was added a solution of cycloheptylamine (0.5 mL, 3.8 mmol) in acetone (5 mL) followed by addition of 2.5 N NaOH (1.5 mL, 3.8 mmol) and water (4 mL). The reaction mixture was allowed to stir at reflux for 3 hours under nitrogen. The reaction mixture was extracted 3 times with dichloromethane; the combined organic layers were washed with brine and dried over sodium sulfate. The filtered sample was concentrated on the rotary evaporator and the resulting solid was dried overnight under vacuum. Flash column chromatography (SiO2, 90:9:1 dichloromethane:methanol:conc. ammonium hydroxide) yielded a white solid (155b, 856 mg, 66%), mp>210° C.; HPLC: Inertsil ODS-3V C18, 40:10:50 [KH2PO4 (0.01M, pH 3.2): CH3OH: CH3CN], 264 nm, Rt 10.0 min, 96.0% purity; MS (TOF MS ES+): m/z 342 (51.5), 341 (35.1), 340 (M+H, 100).

Workup

  1. temperatureat reflux for 3 hours under nitrogen
  2. extractionThe reaction mixture was extracted 3 times with dichloromethane
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationThe filtered sample was concentrated on the rotary evaporator
  6. customthe resulting solid was dried overnight under vacuum

Sources & evidence

ORD record
ord-b11fab8c1c86474db0e11ca13142ab93
Source dataset
uspto-grants-2008_02
Patent number
US07335770B2

Reaction notes

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