Cyclohexanemethylamine → HCID 67384463, compound

HRID 2360986Notes

Reaction equation

HRID 2360986 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24](=[O:26])[NH2:25])=[CH:20][CH:19]=2)([C:14]([OH:16])=O)[CH2:10][CH2:9]1)=O)(C)(C)C.[CH:27]1([CH2:33][NH2:34])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]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:27]1([CH2:33][NH:34][C:14]([C:11]2([CH2:17][C:18]3[CH:19]=[CH:20][C:21]([C:24](=[O:26])[NH2:25])=[CH:22][CH:23]=3)[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[O:16])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

6

Reactant 4

HCID 76688CyclohexanemethylamineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67384766HCID 67384766, compound

Product 1

HCID 67384463HCID 67384463, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of solution of 4-(4-carbamoylbenzyl)-piperidine-1,4-dicarboxylic acid mono-tert-butyl ester (1.38 mmol; 0.5 g) in DMF (5 mL) was added cyclohexylmethylamine (1.18 mmol; 0.154 mL), N,N-diisopropyl-N-ethylamine (2.81 mmol; 0.50 mL) and HBTU (1.38 mmol; 0.51 g), and the resulting mixture was stirred at room temperature overnight. The mixture was purified via reverse phase HPLC. The desired fractions were combined and lyophilized. The residue was dissolved in tetrahydrofuran (2 mL) and a 4N HCl in 1,4-dioxane solution (3 mL), and the resulting mixture was stirred for 4 hours at room temperature and evaporated. The residue was triturated with diethyl ether and dried under vacuum to yield 4-(4-carbamoylbenzyl)-piperidine-4-carboxylic acid cyclohexylmethyl amide as a hydrochloride salt. MS (ESI) m/z 358.40 [M+H]+.

Workup

  1. customThe mixture was purified via reverse phase HPLC
  2. dissolutionThe residue was dissolved in tetrahydrofuran (2 mL)
  3. stirringa 4N HCl in 1,4-dioxane solution (3 mL), and the resulting mixture was stirred for 4 hours at room temperature
  4. customevaporated
  5. customThe residue was triturated with diethyl ether
  6. customdried under vacuum

Sources & evidence

ORD record
ord-7ccace04906a42ce8463c74466dde551
Source dataset
uspto-grants-2014_04
Patent number
US08686152B2

Reaction notes

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