4-Piperidinamine → HCID 10752643, compound

HRID 1442647Notes

Reaction equation

HRID 1442647 reaction equation
N1CCC(N)CC1.[N+:8]([C:11]1[CH:24]=[CH:23][C:14]([CH2:15][N:16]2[CH2:21][CH2:20][CH:19]([NH2:22])[CH2:18][CH2:17]2)=[CH:13][CH:12]=1)([O-])=O>CO.[Rh]>[NH2:8][C:11]1[CH:12]=[CH:13][C:14]([CH2:15][N:16]2[CH2:17][CH2:18][CH:19]([NH2:22])[CH2:20][CH2:21]2)=[CH:23][CH:24]=1

Participants

5

Reactant 2

HCID 4243614-PiperidinamineHCID 10823651HCID 10823651, compound2×

Product 1

HCID 10752643HCID 10752643, compound

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 887MethanolSolvent

Procedure

Using the procedure of Example 1, piperidin-4-ylamine Compound 21a1 was used in place of Compound 1n2 and carried forward to prepare 1-(4-nitro-benzyl)-piperidin-4-ylamine Compound 21a2. 5% Rh/C (350 mg) was added to a solution of 1-(4-nitrobenzyl)-piperidin-4-ylamine Compound 21a2 (647 mg, 2.75 mmol) in methanol (15 mL). The mixture was hydrogenated at 50 PSI for a period of 2 hrs, then filtered through Celite. The filtrate was evaporated in vacuo to give 1-(4-amino-benzyl)-piperidin-4-ylamine Compound 21a (640 mg) as a light yellow oil. 1H NMR (CDCl3) δ 7.09 (d, J=8.2 Hz, 2H); 6.64 (d, J=8.2 Hz, 2H); 3.62 (br s, 1H); 3.41 (s, 2H); 2.88-2.80 (m, 2H); 2.70-2.58 (m, 1H); 2.07-1.95 (m, 2H); 1.84-1.74 (m, 2H); 1.57 (br s, 2H); 1.47-1.32 (m, 2H); 1.31-1.18 (m, 2H).

Workup

  1. filtrationfiltered through Celite
  2. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-00b6e5ec7e47486d81854d143153c61f
Source dataset
uspto-grants-2010_02
Patent number
US07659284B2

Reaction notes

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