Piperazine → HCID 18186780, compound

HRID 1296672Notes

Reaction equation

HRID 1296672 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([O:8][CH2:9][CH2:10][O:11][C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][C:16]([O:22][CH3:23])=[CH:17][CH:18]=3)[CH:13]=2)[N:3]=1.[CH3:24][O:25][C:26]1[CH:35]=[C:34]2[C:29]([CH:30]=[CH:31][C:32]([O:36][CH2:37][CH2:38][OH:39])=[CH:33]2)=[CH:28][CH:27]=1.[NH:40]1[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1.C([O-])([O-])=O.[K+].[K+].COC1C=C2C(C=CC(O)=C2)=CC=1.C1(=O)OCCO1>>[CH3:23][O:22][C:16]1[CH:15]=[C:14]2[C:19]([CH:20]=[CH:21][C:12]([O:11][CH2:10][CH2:9][O:8][C:4]3[CH:5]=[N:6][CH:7]=[C:2]([N:40]4[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]4)[N:3]=3)=[CH:13]2)=[CH:18][CH:17]=1.[CH3:24][O:25][C:26]1[CH:35]=[C:34]2[C:29]([CH:30]=[CH:31][C:32]([O:36][CH2:37][CH2:38][OH:39])=[CH:33]2)=[CH:28][CH:27]=1

Participants

8

Reactant 6

HCID 4837PiperazineHCID 7303Ethylene carbonateHCID 11430Potassium CarbonateHCID 8531737-Methoxy-2-naphtholHCID 18186775HCID 18186775, compoundHCID 18186865HCID 18186865, compound

Product 2

HCID 18186780HCID 18186780, compoundHCID 18186865HCID 18186865, compound

Procedure

The title compound was prepared according to the procedure of example 50, step 2, starting from 2-chloro-6-[2-(7-methoxy-naphthalen-2-yloxy)-ethoxy]pyrazine [1.19 g, 3.60 mmol; obtained according to the procedure of example 50, step 1, starting from 2-(7-methoxy-naphthalen-2-yloxy)ethanol*], piperazine (1.25 g, 14.5 mmol) and K2CO3 (0.60 g, 4.3 mmol) with the exception that the final filtration through alumina was omitted. The yield of the of the title compound was 0.98 g (71%) which was obtained as an oil that solidified when refrigerated. Purity 100% (HPLC). MS m/z 380 (M)+. HRMS m/z calcd for C21H24N4O3 (M)+0 380.1848, found 380.1851. *Prepared from 7-methoxy-2-naphthol and ethylene carbonat according to the procedure of Example 134, step 1, in WO 00/76984. The reaction mixture was refluxed for 2 h. Pure 2-(7methoxy-naphthalen-2-yloxy)ethanol was obtained after column chromatography on silica gel using n-hexane/ethyl acetate (6:4) as eluent.

Workup

  1. customobtained
  2. filtrationfiltration through alumina
  3. customwas obtained as an oil that solidified when refrigerated
  4. temperatureThe reaction mixture was refluxed for 2 h

Sources & evidence

ORD record
ord-73274cbacb9d4ce6aa76e1850368f1c7
Source dataset
uspto-grants-2007_07
Patent number
US07247633B2

Reaction notes

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