Benzhydrylpiperazine → HCID 23289343, compound

HRID 366423Notes

Reaction equation

HRID 366423 reaction equation
[CH:1]([N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:21][CH2:22][O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C:30]1[S:31][C:32]2[CH:38]=[CH:37][CH:36]=[CH:35][C:33]=2[N:34]=1>CC(O)(C)C>[CH:1]([N:14]1[CH2:19][CH2:18][N:17]([CH2:21][CH2:22][O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:30]2[S:31][C:32]3[CH:38]=[CH:37][CH:36]=[CH:35][C:33]=3[N:34]=2)[CH2:16][CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70048BenzhydrylpiperazineHCID 23289280HCID 23289280, compound

Product 1

HCID 23289343HCID 23289343, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

1-Benzhydryl-piperazine (2.26 g, 8.98 mmol) and 2-[2-(2-bromoethoxy)phenyl]-benzothiazole (0.75 g, 2.24 mmol) were stirred in t-BuOH (20 mL) at about 50° C. under N2 (g) for 24 hours. The mixture was concentrated in vacuo and flash chromatographed on silica (15% acetone/hexanes) to afford 460 mg (41%) of the free base of the product. mp 67-72° C.; LSIMS m/z 506 (MH+).

Workup

  1. concentrationThe mixture was concentrated in vacuo and flash
  2. customchromatographed on silica (15% acetone/hexanes)

Sources & evidence

ORD record
ord-53dd29f0c17a4b4f9c739c41324802b2
Source dataset
uspto-grants-2000_10
Patent number
US06130217

Reaction notes

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