(1R,2S)-Tranylcypromine → HCID 66571590, compound

HRID 534155

Reaction equation

HRID 534155 reaction equation
[C:1]1([C@@H:7]2[CH2:9][C@H:8]2[NH2:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:11][N:12]1[CH2:17][CH2:16][CH:15]([CH:18]=O)[CH2:14][CH2:13]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl.CC(O)=O>[CH3:11][N:12]1[CH2:17][CH2:16][CH:15]([CH2:18][NH:10][C@@H:8]2[CH2:9][C@H:7]2[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:14][CH2:13]1

Participants

7

Reactant 4

HCID 19493(1R,2S)-TranylcypromineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 125352281-Methylpiperidine-4-carbaldehyde

Product 1

HCID 66571590HCID 66571590, compoundYield 17.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6212ChloroformSolvent

Procedure

A mixture of [trans-2-phenylcyclopropyl]amine (540 mg, 4.05 mmol), 1-methyl-4-piperidinecarbaldehyde (506 mg, 3.98 mmol) and AcOH (l μL, 0.017 mmol) in chloroform (15 mL) was stirred at room temperature for 18 hours. Sodium triacetoxyborohydride (947 mg, 4.47 mmol) was added and stirring continued for 18 hours. Upon completion, saturated NaHCO3 was added to the reaction mixture and the mixture was extracted with THF—CHCl3 (2×50mL). The organics were combined, dried over Na2SO4 and concentrated. The residue was adsorbed onto silica and purified via column chromatography on the ISCO Companion (gradient 0-100% 80:20:2 [CHCl3/MeOH/NH4OH]/CHCl3; 40 g column) to obtain pure final compound (166 mg, 13% yield) as an off white solid: LC-MS (ES) m/z=245 (M+H)+, 1H NMR (400 MHz, DMSO-d6) δ ppm 7.17-7.27 (m, 2H), 7.06-7.15 (m, 1H), 6.97-7.06 (m, 2H), 2.64-2.77 (m, 2H), 2.41-2.49 (m, 2H), 2.27 (br. s., 1H), 2.18 (ddd, J=3.28, 4.23, 7.14 Hz, 1H), 2.08-2.15 (m, 3H), 1.70-1.83 (m, 2H), 1.57-1.70 (m, 2H), 1.30 (ddd, J=4.29, 7.26, 10.93 Hz, 1H), 1.01-1.16 (m, 2H), 0.86-0.98 (m, 2H).

Workup

  1. stirringstirring
  2. waitcontinued for 18 hours
  3. extractionthe mixture was extracted with THF—CHCl3 (2×50mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. custompurified via column chromatography on the ISCO Companion (gradient 0-100% 80:20:2 [CHCl3/MeOH/NH4OH]/CHCl3; 40 g column)

Sources & evidence

ORD record
ord-d4d241efb97745f6b0070cf2b80254c5
Source dataset
uspto-grants-2014_10
Patent number
US08853408B2

Linked notes

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