HCID 698982, compound → (4-Aminophenyl)(4-phenylpiperazin-1-yl)methanone

HRID 2380960Notes

Reaction equation

HRID 2380960 reaction equation
O.O.[Sn](Cl)(Cl)(Cl)Cl.[N+:8]([C:11]1[CH:16]=[CH:15][C:14]([C:17]([N:19]2[CH2:24][CH2:23][N:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:21][CH2:20]2)=[O:18])=[CH:13][CH:12]=1)([O-])=O>Cl.C(OCC)C>[NH2:8][C:11]1[CH:12]=[CH:13][C:14]([C:17]([N:19]2[CH2:24][CH2:23][N:22]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH2:21][CH2:20]2)=[O:18])=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 698982HCID 698982, compoundHCID 85782573Tin tetrachloride dihydrate

Product 1

HCID 12932882(4-Aminophenyl)(4-phenylpiperazin-1-yl)methanoneYield 74.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of tin chloride dihydrate (5.44 g, 24.1 mmol) in concentrated hydrochloric acid (32 ml) was added slowly to a cooled, stirred solution of (4-nitro-phenyl)-(4-phenyl-piperazin-1-yl)-methanone (1.0 g, 3.2 mmol) in anhydrous diethyl ether (32 ml). The resulting mixture was stirred for 1 hour at room temperature, then cooled and quenched carefully with 10M sodium hydroxide (aq.) until slightly basic (˜pH 9). The aqueous mixture was extracted with ethyl acetate (100 ml) and the organic extracts dried over magnesium sulfate then concentrated in vacuo to the title compound as a cream solid (667 mg, 73% yield). HPLC retention time 6.2 min. Mass spectrum (ES+) m/z 282 (M+H).

Workup

  1. temperaturecooled
  2. customquenched carefully with 10M sodium hydroxide (aq.) until slightly basic (˜pH 9)
  3. extractionThe aqueous mixture was extracted with ethyl acetate (100 ml)
  4. dry with materialthe organic extracts dried over magnesium sulfate

Sources & evidence

ORD record
ord-8cdd05f7aaaf4c118b6207ea00908eaa
Source dataset
uspto-grants-2012_09
Patent number
US08258138B2

Reaction notes

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