Benzhydrylpiperazine → 1-Benzhydryl-4-(3-((phenylsulfonyl)methyl)oxetan-3-yl)piperazine

HRID 1430862Notes

Reaction equation

[C:1]1([S:7]([CH:10]=[C:11]2[CH2:14][O:13][CH2:12]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:15]([N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CO>[CH:15]([N:28]1[CH2:33][CH2:32][N:31]([C:11]2([CH2:10][S:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)(=[O:9])=[O:8])[CH2:14][O:13][CH2:12]2)[CH2:30][CH2:29]1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A clear solution of 3-((phenylsulfonyl)methylene)oxetane (450 mg, 1.284 mmol) in methanol (10 mL) was treated with 1-benzhydrylpiperazine (389 mg, 1.541 mmol) and stirred at 50° C. overnight, more 3-((phenylsulfonyl)methylene)oxetane (100 mg) was added, stirred at 50° C. o/n, concentrated. The crude was purified by ISCO (40 g), eluted with EA:HX=0-50%, the deired fractions were concentrated to yield 1-benzhydryl-4-(3-((phenylsulfonyl)methyl)oxetan-3-yl)piperazine (670 mg) as a white solid.

Workup

stirringstirred at 50° C. o/n,
concentrationconcentrated
customThe crude was purified by ISCO (40 g)
washeluted with EA
concentrationHX=0-50%, the deired fractions were concentrated

Sources & evidence

ORD record: ord-833c1f6d5edd4c72994c6071d123a492
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940736B2

Reaction notes

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