Trifluoroacetic acid → HCID 178457240, compound

HRID 25541Notes

Reaction equation

HRID 25541 reaction equation
C(O[C:6](=O)[N:7]([C@H:9]1[CH2:14][CH2:13][C@H:12]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][N:20]([CH2:22][CH:23]=[CH2:24])[CH3:21])[CH2:11][CH2:10]1)C)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:22]([N:20]([CH3:21])[CH2:19][CH2:18][CH2:17][CH2:16][O:15][C@H:12]1[CH2:13][CH2:14][C@H:9]([NH:7][CH3:6])[CH2:10][CH2:11]1)[CH:23]=[CH2:24]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178457241HCID 178457241, compound

Product 1

HCID 178457240HCID 178457240, compoundYield 91.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.1 g (5.9 mmol) trans-(4-[4-(Allyl-methyl-amino)-butoxy]-cyclohexyl)-methyl-carbamic acid tert-butyl ester in 28 ml CH2Cl2 were treated with 6 ml TFA at 0° C. for 1 h, the mixture was concentrated in vacuo and dissolved in EtOAc and saturated aqueous NaHCO3 solution. The phases were separated and the inorganic phase was extracted with EtOAc, the combined organic phases were washed with brine, dried over Na2SO4 and evaporated to yield 1.38 g (91%) trans-(4-[4-(Allyl-methyl-amino)-butoxy]-cyclohexyl)-methyl-amine as yellow oil, MS: 255 (MH+).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. dissolutiondissolved in EtOAc
  3. customThe phases were separated
  4. extractionthe inorganic phase was extracted with EtOAc
  5. washthe combined organic phases were washed with brine
  6. dry with materialdried over Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-14e76c67d38b411d9af3b1c13867b9ec
Source dataset
uspto-grants-2005_02
Patent number
US06858651B2

Reaction notes

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