Hydrochloric Acid → HCID 21897054, compound

HRID 1374002Notes

Reaction equation

HRID 1374002 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-d6f795ad6fde4c159cfb36147aef18cf
Source dataset
uspto-grants-2007_01
Patent number
US07163943B2

Reaction notes

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