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Piperazine → HCID 18186793, compound

HRID 1296671
Notes
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Reaction equation

HRID 1296671 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][CH:16]=[C:17]([O:22][CH3:23])[CH:18]=3)[CH:13]=2)[N:3]=1.[CH3:24][O:25][C:26]1[CH:27]=[C:28]2[C:33](=[CH:34][CH:35]=1)[CH:32]=[C:31]([O:36][CH2:37][CH2:38][OH:39])[CH:30]=[CH:29]2.[NH:40]1[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1.C([O-])([O-])=O.[K+].[K+].COC1C=C2C(=CC=1)C=C(O)C=C2.C1(=O)OCCO1>CO.C(Cl)(Cl)Cl.CCCCCC>[CH3:23][O:22][C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[C:12]([O:11][CH2:10][CH2:9][O:8][C:4]1[CH:5]=[N:6][CH:7]=[C:2]([N:40]3[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]3)[N:3]=1)[CH:21]=[CH:20]2.[CH3:24][O:25][C:26]1[CH:27]=[C:28]2[C:33](=[CH:34][CH:35]=1)[CH:32]=[C:31]([O:36][CH2:37][CH2:38][OH:39])[CH:30]=[CH:29]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 6

HCID 4837PiperazineHCID 7303Ethylene carbonateHCID 11430Potassium CarbonateHCID 2886346-Methoxy-2-naphtholHCID 18186793HCID 18186793, compoundHCID 18186892HCID 18186892, compound

Product 2

HCID 18186793
HCID 18186793, compound
HCID 18186912HCID 18186912, compound

Reagents, catalysts & solvents 1

HCID 22285155HCID 22285155, compoundSolvent

Procedure

The title compound was prepared according to the procedure of example 50, step 2, starting from 2-chloro-6-[2-(6-methoxy-naphthalen-2-yloxy)-ethoxy]pyrazine [0.94 g, 2.8 mmol; obtained according to the procedure of example 50, step 1, starting from 2-(6-methoxy-naphthalen-2-yloxy)ethanol*], piperazine (1.00 g, 11.6 mmol) and K2CO3 (0.50 g, 3.6 mmol) with the exception that the final filtration through alumina was omitted. The yield of the of the title compound was 0.52 g (48%) which was obtained as a beige colored solid. Purity 100% (HPLC). MS m/z 380 (M)+. HRMS m/z calcd for C21H24N4O3 (M)+ 380.1848, found 380.1845. *Prepared from 6-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-(6-methoxy-naphthalen-2-yloxy)ethanol was obtained by recrystallization from MeOH/CHCl3/n-hexane.

Workup

  1. customobtained
  2. filtrationfiltration through alumina
  3. customwas obtained as a beige colored solid
  4. temperatureThe reaction mixture was refluxed for 2 h

Sources & evidence

ORD record
ord-2225d59e48f34390a1740d04b5ebec30
Source dataset
uspto-grants-2007_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07247633B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes