HCID 178418361, compound → HCID 178511722, compound

HRID 2111579Notes

Reaction equation

HRID 2111579 reaction equation
C([N:8](CC1C=CC=CC=1)[C@H:9]1[CH2:14][CH2:13][C@H:12]([O:15][CH2:16][CH2:17][N:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[CH2:11][CH2:10]1)C1C=CC=CC=1.[H][H]>[OH-].[OH-].[Pd+2].CO>[N:18]1([CH2:17][CH2:16][O:15][C@H:12]2[CH2:11][CH2:10][C@H:9]([NH2:8])[CH2:14][CH2:13]2)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178420356HCID 178420356, compound

Product 1

HCID 178511722HCID 178511722, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

Trans-N,N-dibenzyl-4-(2-(piperidin-1-yl)ethoxy)cyclohexanamine (4.7 g, 11.6 mmol), 20% Pd(OH)2/C (0.94 g) and methanol (40 mL) were charged into a septum-sealed flask. The reaction mixture was placed under balloon pressure of hydrogen for 18 h at ambient temperature, at which time LCMS indicated complete debenzylation to form the free amine. The catalyst was filtered off and the filtrate evaporated under reduced pressure to give 2.42 g of a crystalline material (93%). In some cases an additional portion of catalyst (ca. 50% of the initial charge) was needed in order to attain complete reaction. LRMS (ES) m/e 227.2 [MH]+; 1H NMR (300 MHz, CD3OD) δ 3.51(t, 2H), 3.12(m, 1H), 2.61(m, 1H), 2.42(t, 2H), 2.18(m, 4H), 1.93(m, 2H), 1.80(m, 2H), 1.50(m, 4H), 1.33(m, 2H), 1.12(m, 4H).

Sources & evidence

ORD record
ord-d6cc3112999c49ea85ceaaa80d6001a1
Source dataset
uspto-grants-2009_04
Patent number
US07521446B2

Reaction notes

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