Piperazine → HCID 12150200, compound

HRID 991529Notes

Reaction equation

HRID 991529 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, 41H).

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. customIt was collected by,
  5. filtrationfiltration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-e55a4e604c044d42a3eba1755c2fb4c8
Source dataset
uspto-grants-2002_10
Patent number
US06465472B1

Reaction notes

Loading…