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

HRID 410342Notes

Reaction equation

HRID 410342 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH2:20][C:19]([CH3:22])([CH3:21])[CH2:18][CH2:17][C:16]=2[C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[Cl:29][C:26]1[CH:27]=[CH:28][C:23]([C:16]2[CH2:17][CH2:18][C:19]([CH3:21])([CH3:22])[CH2:20][C:15]=2[CH2:14][N:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 672260044-[2-(4-Chloro-phenyl)-5,5-dimethyl-cyclohex-1-enylmethyl]-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 585649441-((4'-Chloro-4,4-dimethyl-3,4,5,6-tetrahydro-[1,1'-biphenyl]-2-yl)methyl)piperazineYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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]+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionA saturated solution of NaHCO3 was added
  3. extractionthe mixture was extracted with dichloromethane (×2)
  4. washThe combined extracts were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2c790d8bc74e4c70b9571c3461e909e8
Source dataset
uspto-grants-2014_06
Patent number
US08759520B2

Reaction notes

Loading…