Cyclohexanemethylamine → HCID 86657552, compound

HRID 2360991Notes

Reaction equation

HRID 2360991 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([C:17]2[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[C:19]([C:27]([F:30])([F:29])[F:28])[CH:18]=2)([C:14](O)=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C.[CH:31]1([CH2:37][NH2:38])[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1.C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH:31]1([CH2:37][NH:38][C:14]([C:11]2([C:17]3[CH:18]=[C:19]([C:27]([F:29])([F:28])[F:30])[CH:20]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:22]=3)[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[O:15])[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

6

Reactant 4

HCID 76688CyclohexanemethylamineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86657553HCID 86657553, compound

Product 1

HCID 86657552HCID 86657552, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(3,5-bis-trifluoromethylphenyl)-piperidine-1,4-dicarboxylic acid mono-tert-butyl ester (0.5 mmol; 220.7 mg) in DMF (2 mL) was added cyclohexylmethylamine (0.6 mmol; 0.078 mL), N, N-diisopropyl-N-ethylamine (1 mmol; 0.174 mL) and HBTU (0.6 mmol; 228 mg), and the resulting mixture was stirred at room temperature overnight. The mixture was then purified via reverse phase HPLC. The desired fractions were combined and lyophilized. The resulting residue was dissolved in 1,4-dioxane (3 mL) and a 4N HCl solution in 1,4-dioxane (3 mL) was added. The resulting mixture was stirred for 2 hours at room temperature, then evaporated to yield 4-(3,5-bis-trifluoromethylphenyl)-piperidine-4-carboxylic acid cyclohexylmethylamide as a hydrochloride salt. MS (ESI) m/z 437.3 [M+H]+.

Workup

  1. customThe mixture was then purified via reverse phase HPLC
  2. dissolutionThe resulting residue was dissolved in 1,4-dioxane (3 mL)
  3. additiona 4N HCl solution in 1,4-dioxane (3 mL) was added
  4. stirringThe resulting mixture was stirred for 2 hours at room temperature
  5. customevaporated

Sources & evidence

ORD record
ord-410f9740844d48ab809484b7f851cfca
Source dataset
uspto-grants-2014_04
Patent number
US08686152B2

Reaction notes

Loading…