Piperazine → HCID 12150200, compound

HRID 1884383Notes

Reaction equation

HRID 1884383 reaction equation
Cl[CH2:2][C:3]1[N:12]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]3[O:19][CH2:20][O:21][C:15]=3[CH:14]=2)[C:10]2[C:5](=[CH:6][C:7]3[O:24][CH2:23][O:22][C:8]=3[CH:9]=2)[N:4]=1.[NH:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1>CCO>[CH2:23]1[O:24][C:7]2[CH:6]=[C:5]3[C:10]([C:11]([C:13]4[CH:18]=[CH:17][C:16]5[O:19][CH2:20][O:21][C:15]=5[CH:14]=4)=[N:12][C:3]([CH2:2][N:25]4[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]4)=[N:4]3)=[CH:9][C:8]=2[O:22]1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 12150202HCID 12150202, compound

Product 1

HCID 12150200HCID 12150200, compoundYield 62.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 2-chloromethyl-6,7-methylenedioxy-4-(3,4-methylenedioxy-phenyl)quinazoline (96 mg, 0.3 mmol) in EtOH (9 mL) was treated with piperazine (860 mg, 10 mmol). The mixture was stirred at rt for 15 h, then it was poured into ice cold dilute NaHCO3 solution. On standing at rt for 72 h the title compound was crystallized out as colorless plates. It was collected by filtration, washed with water, and dried to give 74 mg of solid; mp 73-76° C. 1H NMR (CDCl3) 7.37 (d, J=8.4, 1H), 7.16-7.24 (m, 3H), 6.97 (d, J=8.4, 1H), 6.14 (s, 2H), 6.07 (s, 2H), 3.95 (s, 2H), 2.97 (bs, 4H), 2.65 (bs, 4H).

Workup

  1. additionit was poured into ice cold dilute NaHCO3 solution
  2. waitOn standing at rt for 72 h
  3. customthe title compound was crystallized out as colorless plates
  4. filtrationIt was collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-080d4daa4ee94932af8688ffcc161f4f
Source dataset
uspto-grants-2004_07
Patent number
US06765006B2

Reaction notes

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