Benzhydrylpiperazine → HCID 23289356, compound

HRID 366422Notes

Reaction equation

HRID 366422 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.[O:20]1[CH2:22][CH:21]1[CH2:23][O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:31]1[S:32][C:33]2[CH:39]=[CH:38][CH:37]=[CH:36][C:34]=2[N:35]=1>CCO>[CH:1]([N:14]1[CH2:19][CH2:18][N:17]([CH2:22][CH:21]([OH:20])[CH2:23][O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:31]2[S:32][C:33]3[CH:39]=[CH:38][CH:37]=[CH:36][C:34]=3[N:35]=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 23289243HCID 23289243, compound

Product 1

HCID 23289356HCID 23289356, compoundYield 42.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-benzhydryl-piperazine (891 mg, 3.53 mmol) and 2-[2-(oxiran-2-yl-methoxy)phenyl]benzothiazole (1000 mg, 3.53 mmol) in EtOH (7 mL) were refluxed under N2 (g) for about 16 hours. The mixture was concentrated in vacuo to a white foam and flash chromatographed on silica (35% EtOAc/hexanes) to afford 807 mg (42%) of the free base of the product as a white solid. mp 152-155° C.; LSIMS m/z 536 (MH+).

Workup

  1. concentrationThe mixture was concentrated in vacuo to a white foam and flash
  2. customchromatographed on silica (35% EtOAc/hexanes)

Sources & evidence

ORD record
ord-0b1022d8be3f48e0b0067d4b000fd6ce
Source dataset
uspto-grants-2000_10
Patent number
US06130217

Reaction notes

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