4-Amino-1-methylpiperidine → Ammonium Hydroxide

HRID 2243670Notes

Reaction equation

HRID 2243670 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]2[N:15]=[C:16](S(C)(=O)=O)[N:17]=[C:18]([C:19]3[CH:20]=[C:21]([CH:32]=[CH:33][C:34]=3[CH3:35])[C:22]([NH:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:23])[C:13]=2[CH2:12][NH:11][C:10]1=[O:40].[NH2:41][CH:42]1[CH2:47][CH2:46][N:45]([CH3:48])[CH2:44][CH2:43]1>C(Cl)Cl.CCOC(C)=O>[NH4+:9].[OH-:23].[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]2[N:15]=[C:16]([NH:41][CH:42]3[CH2:47][CH2:46][N:45]([CH3:48])[CH2:44][CH2:43]3)[N:17]=[C:18]([C:19]3[CH:20]=[C:21]([CH:32]=[CH:33][C:34]=3[CH3:35])[C:22]([NH:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:23])[C:13]=2[CH2:12][NH:11][C:10]1=[O:40]

Participants

6

Reactant 2

HCID 27375314-Amino-1-methylpiperidine2×HCID 11950098HCID 11950098, compound

Product 2

HCID 14923Ammonium HydroxideHCID 11952413HCID 11952413, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The compound 3-[8-(2,6-difluorophenyl)-2-(methylsulfonyl)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-4-methyl-N-(phenylmethyl)benzamide, (0.06 g, 0.106 mmol) was dissolved in CH2Cl2 (5 mL) and 4-amino-1-methylpiperidine (0.031 g, 0.265 mmol) was added. The mixture was stirred under argon at room temperature for 16 h with some product formation. The reaction was not complete, so additional 4-amino-1-methylpiperidine (0.031 g, 0.265 mmol) was added and the mixture stirred for an additional 24 h. The reaction still was not complete, and was then heated to reflux for 24 h. The solvents were pumped off in vacuo. The residue was taken up in EtOAc washed with 1M NaOH (2×), brine (1×), dried over anhydrous Na2SO4, filtered and evaporated The residue was flash chromatographed on silica gel (20 g) eluted with 6:2:0.2, CH2Cl2:ethanol:NH4OH to give the title compound as a white amorphous solid. mp (dec) 152-154° C.; LC-MS m/z 598 (M+H)+, 1.62 min (ret. time).

Workup

  1. stirringthe mixture stirred for an additional 24 h
  2. customThe reaction
  3. temperaturewas then heated
  4. temperatureto reflux for 24 h
  5. washwashed with 1M NaOH (2×), brine (1×)
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. customevaporated The residue
  9. customchromatographed on silica gel (20 g)
  10. washeluted with 6:2:0.2, CH2Cl2

Sources & evidence

ORD record
ord-435da9686a6d4e3a8161c4fe7f7c0a15
Source dataset
uspto-grants-2010_03
Patent number
US07674789B2

Reaction notes

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