Piperazine → 2-Piperazin-1-yl-1,3-benzothiazole

HRID 1769531Notes

Reaction equation

HRID 1769531 reaction equation
Cl[C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[NH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1>>[N:11]1([C:2]2[S:3][C:4]3[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=3[N:6]=2)[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1

Participants

3

Reactant 2

HCID 4837PiperazineHCID 119872-Chlorobenzothiazole

Product 1

HCID 5921222-Piperazin-1-yl-1,3-benzothiazole

Procedure

2-Chlorobenzothiazole (5.00 g), is heated in alcohol (75 ml) with 3.05 g piperazine (3.05 g) for 20 hr. The mixture is partitioned between methylene chloride/ether and aqueous sodium bicarbonate, the phases are separated, the organic phase is dried with sodium sulfate and concentrated to give 2-piperazinobenzothiazole which is reacted at 70° in acetonitrile (200 ml) with 21-bromo-17α-hydroxypregna-4,9(11)-diene-3,20-dione (7.45 g) and potassium carbonate (2.44 g) for 6 hr and at 20°-25° for 3 days. The mixture is partitioned between methylene chloride and aqueous sodium bicarbonate, the phases are separated, the organic phase is dried with sodium sulfate and concentrated. The concentrate is chromatographed on silica gel eluting with methanol/methylene chloride (6/94) to give the title compound which is recrystallized from ethyl acetate.

Workup

  1. customThe mixture is partitioned between methylene chloride/ether and aqueous sodium bicarbonate
  2. customthe phases are separated
  3. dry with materialthe organic phase is dried with sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ac55958a70d54ae5b45e10a563990d08
Source dataset
uspto-grants-1995_01
Patent number
US05380841

Reaction notes

Loading…