Hydrochloric Acid → 1-[3-(Trifluoromethoxy)phenyl]piperazin-2-one--hydrogen chloride (1/1)

HRID 1935400Notes

Reaction equation

HRID 1935400 reaction equation
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7].[ClH:13].[C:14]([C:16]1[CH:29]=[CH:28][C:19]([CH2:20][N:21]2[C:25]([CH:26]=[O:27])=[CH:24][N:23]=[CH:22]2)=[CH:18][C:17]=1[O:30][CH3:31])#[N:15]>>[ClH:13].[F:1][C:2]([F:11])([F:12])[O:3][C:4]1[CH:5]=[C:6]([N:7]2[CH2:19][CH2:20][NH:21][CH2:25][C:26]2=[O:27])[CH:8]=[CH:9][CH:10]=1.[ClH:13].[ClH:13].[F:1][C:2]([F:11])([F:12])[O:3][C:4]1[CH:5]=[C:6]([N:7]2[CH2:19][CH2:20][N:21]([CH2:26][C:25]3[N:21]([CH2:20][C:19]4[CH:28]=[CH:29][C:16]([C:14]#[N:15])=[C:17]([O:30][CH3:31])[CH:18]=4)[CH:22]=[N:23][CH:24]=3)[CH2:25][C:26]2=[O:27])[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 737533-(Trifluoromethoxy)anilineHCID 22464402HCID 22464402, compound

Product 2

HCID 224643741-[3-(Trifluoromethoxy)phenyl]piperazin-2-one--hydrogen chloride (1/1)HCID 22464395HCID 22464395, compound

Procedure

1-(3-trifluoromethoxy-phenyl)-2-piperazinone hydrochloride was prepared from 3-trifluoromethoxyaniline using Steps F-J of Example 1. This amine (1.75 g, 5.93 mmol) was coupled to the aldehyde from Step I of Example 6 (1.57 g, 6.52 mmol) using the procedure outlined in Step H of Example 1. Purification by flash column chromatography through silica gel (60%-100% acetone CH2Cl2) and conversion of the resulting white foam to its dihydrochloride salt provided the titled product as a white powder.

Workup

  1. customPurification by flash column chromatography through silica gel (60%-100% acetone CH2Cl2) and conversion of the resulting white foam to its dihydrochloride salt

Sources & evidence

ORD record
ord-f3921fe63d0e4a1b8875c89263ca46cc
Source dataset
uspto-grants-2002_05
Patent number
US06387903B1

Reaction notes

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