Water → HCID 10390493, compound

HRID 915142Notes

Reaction equation

HRID 915142 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[N:14]=[C:13](Cl)[N:12]=[C:11]([NH:16][CH:17]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[N:10]=2)[CH:5]=[CH:4][C:3]=1[OH:24].[CH3:25][N:26]1[CH2:31][CH2:30][CH:29]([NH:32][CH3:33])[CH2:28][CH2:27]1.[OH-].[Na+].O>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[N:10]=[C:11]([NH:16][CH:17]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[N:12]=[C:13]([N:32]([CH3:33])[CH:29]3[CH2:30][CH2:31][N:26]([CH3:25])[CH2:27][CH2:28]3)[N:14]=2)[CH:5]=[CH:4][C:3]=1[OH:24]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 5663231-Methyl-4-(methylamino)piperidineHCID 21897094HCID 21897094, compound

Product 1

HCID 10390493HCID 10390493, compoundYield 14.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To E7 (1.00 g, 2.7 mmol) dissolved in THF (25 mL) was added a solution of N-methyl-4-(methylamino)-piperidine (0.45 mL, 3.1 mmol) in THF (5 mL) followed by addition of 2.5 N NaOH (1.1 mL, 2.7 mmol) and 2.5 mL of water. The reaction mixture was stirred and heated at reflux overnight. The reaction mixture was extracted three times using dichloromethane, the combined organic layers were washed with a brine and dried over sodium sulfate. The sample was concentrated and the resulting solid was dried overnight under vacuum. Column chromatography (silica gel, 100% methanol) yielded an off-white solid (138) (177 mg, 14%); mp 68° C.; HPLC: Inertsil ODS 3V C18, 40:30:30 v:v:v [KH2PO4 (0.01 M, pH 3.2):CH3OH:CH3CN], 264 nm, Rt 4.7 min, 99.6% purity; MS (TOF ES+) m/z 460 (M+H, 55.3), 251 (100), 224 (51.1).

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. extractionThe reaction mixture was extracted three times
  4. washthe combined organic layers were washed with a brine
  5. dry with materialdried over sodium sulfate
  6. concentrationThe sample was concentrated
  7. customthe resulting solid was dried overnight under vacuum

Sources & evidence

ORD record
ord-980fa993c36f4e748e13c5039d67b736
Source dataset
uspto-grants-2007_09
Patent number
US07265114B2

Reaction notes

Loading…