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

HRID 2209899Notes

Reaction equation

HRID 2209899 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-e4c5760898594739a2ed09e537fae1eb
Source dataset
uspto-grants-1995_10
Patent number
USRE035053

Reaction notes

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