Piperazine → HCID 18186929, compound

HRID 1357637Notes

Reaction equation

HRID 1357637 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([O:8][CH2:9][C:10]2[CH:14]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)[O:12][C:11]=2[CH3:22])[N:3]=1.ClC1C=CC(C2OC(C)=C(CO)C=2)=CC=1.[NH:38]1[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]1.C([O-])([O-])=O.[K+].[K+]>>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([C:13]2[O:12][C:11]([CH3:22])=[C:10]([CH2:9][O:8][C:4]3[CH:5]=[N:6][CH:7]=[C:2]([N:38]4[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]4)[N:3]=3)[CH:14]=2)=[CH:16][CH:17]=1

Participants

5

Reactant 4

HCID 4837PiperazineHCID 11430Potassium CarbonateHCID 7245332[5-(4-Chlorophenyl)-2-methylfuran-3-yl]methanolHCID 18186841HCID 18186841, compound

Product 1

HCID 18186929HCID 18186929, compound

Procedure

The title compound was prepared according to the procedure of example 50, step 2, starting from 2-chloro-6-[5-(4-chlorophenyl)-2-methylfuran-3-ylmethoxy]pyrazine [3.14 g, 9.39 mmol; obtained according to the procedure of example 50, step 1, starting from 5-(4-chlorophenyl)-3-hydroxymethyl-2-methylfuran], piperazine (2.47 g, 28.6 mmol) and K2CO3 (1.36 g, 9.86 mmol) with the exception that the final filtration through alumina was omitted. The yield of the of the title compound was 2.11 g (58%) which was obtained as a beige colored solid. Purity 100% (HPLC). MS m/z 384 (M)+. HRMS m/z calcd for C20H21ClN4O2 (M)+ 384.1353, found 384.1357.

Workup

  1. customobtained
  2. filtrationfiltration through alumina
  3. customwas obtained as a beige colored solid

Sources & evidence

ORD record
ord-e6f35c6d07e24413aefabc6bfbab6242
Source dataset
uspto-grants-2003_07
Patent number
US06593330B2

Reaction notes

Loading…