Hydrochloric Acid → HCID 21897054, compound

HRID 2055339Notes

Reaction equation

HRID 2055339 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([Cl:17])[CH:10]=2)[N:5]=[C:4]([NH:18][CH:19]([CH2:23][CH2:24][CH3:25])[CH2:20][CH2:21][CH3:22])[N:3]=1.[CH3:26][N:27]1[CH2:32][CH2:31][CH:30]([NH:33][CH3:34])[CH2:29][CH2:28]1.[OH-].[Na+].Cl>O1CCOCC1.CC(C)=O>[OH-:15].[NH4+:3].[Cl:17][C:11]1[CH:10]=[C:9]([NH:8][C:6]2[N:7]=[C:2]([N:33]([CH3:34])[CH:30]3[CH2:31][CH2:32][N:27]([CH3:26])[CH2:28][CH2:29]3)[N:3]=[C:4]([NH:18][CH:19]([CH2:23][CH2:24][CH3:25])[CH2:20][CH2:21][CH3:22])[N:5]=2)[CH:14]=[CH:13][C:12]=1[O:15][CH3:16]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 5663231-Methyl-4-(methylamino)piperidineHCID 21897003HCID 21897003, compound

Product 2

HCID 14923Ammonium HydroxideHCID 21897054HCID 21897054, compoundYield 40.8%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a sample of 104 (0.363 g, 1.0 mmol) dissolved in 1,4-dioxane (6 mL) was added a solution of N-methyl-4-(methylamino)piperidine (0.15 mL, 1.0 mmol) in acetone (1 mL) followed by addition of a NaOH solution (0.0414 g, 1.0 mmol dissolved in 1 mL of H2O). The reaction mixture was allowed to stir at about 80° C. for about about 2 hours. The reaction mixture was poured over crushed ice and neutralized with 10% HCl (aq). The resulting solid was collected by vacuum filtration, washed with water and dried under vacuum overnight. Column chromatography (silica gel, 96:3:1 dichloromethane:methanol:conc. ammonium hydroxide) yielded light purple solid 105 (97 mg, 20%), mp 249° C. HPLC: YMC Pack Pro C18, 40:30:30 [KH2PO4 (0.01M, pH 3.2):CH3OH:CH3CN], 264 nm, Rt 14.4 min, 98% purity; MS (ESI): m/z 476 (M+H, 100), 412 (2.9), 366 (2.8), 239 (1.9).

Workup

  1. additionThe reaction mixture was poured
  2. customover crushed ice
  3. filtrationThe resulting solid was collected by vacuum filtration
  4. washwashed with water
  5. customdried under vacuum overnight

Sources & evidence

ORD record
ord-9bb5b7cd5f65444ebd33a2730f059e59
Source dataset
uspto-grants-2008_02
Patent number
US07332489B2

Reaction notes

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