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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 410342Generated: October 31, 2026

Trifluoroacetic acid → 1-((4'-Chloro-4,4-dimethyl-3,4,5,6-tetrahydro-[1,1'-biphenyl]-2-yl)methyl)piperazine

https://huagongshe.com/reaction/410342

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTrifluoroacetic acidHCID 6422—
Reactant4-[2-(4-Chloro-phenyl)-5,5-dimethyl-cyclohex-1-enylmethyl]-piperazine-1-carboxylic acid tert-butyl esterHCID 67226004—
SolventDichloromethaneHCID 6344—
Product1-((4'-Chloro-4,4-dimethyl-3,4,5,6-tetrahydro-[1,1'-biphenyl]-2-yl)methyl)piperazineHCID 58564944100%

Reaction Steps

To a solution of 4-[2-(4-chloro-phenyl)-5,5-dimethyl-cyclohex-1-enylmethyl]-piperazine-1-carboxylic acid tert-butyl ester (1.0 g, 2.39 mmol) in dichloromethane (20 ml) was added TFA (5 ml). The reaction was stirred for 1 h and then concentrated under reduced pressure. A saturated solution of NaHCO3 was added to adjust the pH to ˜8-9 and the mixture was extracted with dichloromethane (×2). The combined extracts were washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure to give 1-[2-(4-chloro-phenyl)-5,5-dimethyl-cyclohex-1-enylmethyl]-piperazine (0.76 g, 100%). HPLC-MS 319, 321 [M+1]+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08759520B2
Source datasetuspto-grants-2014_06
ORD IDord-2c790d8bc74e4c70b9571c3461e909e8
Source noteuspto-grants-2014_06