Benzylamine → 1-(3-(4-Fluorophenoxy)propyl)-3-methoxypiperidin-4-amine

HRID 324685Notes

Reaction equation

HRID 324685 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][CH2:7][CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][C:13](=O)[CH:12]([O:17][CH3:18])[CH2:11]2)=[CH:4][CH:3]=1.C([NH2:28])C1C=CC=CC=1.S1C=CC=C1>C1COCC1.[Pd]>[F:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][CH2:7][CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([NH2:28])[CH:12]([O:17][CH3:18])[CH2:11]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7504BenzylamineHCID 8030ThiopheneHCID 110658701-[3-(4-Fluorophenoxy)propyl]-3-methoxy-4-piperidinone2×

Product 1

HCID 136778321-(3-(4-Fluorophenoxy)propyl)-3-methoxypiperidin-4-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-[3-(4-fluorophenoxy)-propyl]-3-methoxy-4-piperidinone (140 mg, intermediate 1), benzylamine (61 mg), Pd 10% on charcoal (100 mg) and a 0.02% solution of thiophene in THF was reacted under hydrogen gas for 3 hours at 50° C. The catalyst was filtered off and fresh palladium 10% on charcoal (100 mg) was added. Debenzylation of the formed intermediate took place under hydrogen atmosphere for 18 hours at 50° C. The reaction mixture was filtered and evaporated under a gentle stream of nitrogen to yield 1-[3-(4-fluorophenoxy)-propyl]-3-methoxy-4-piperidinamine (compound I-1) having a cis/trans ratio of about 93/7.

Workup

  1. filtrationThe catalyst was filtered off
  2. additionfresh palladium 10% on charcoal (100 mg) was added
  3. customfor 18 hours
  4. customat 50° C
  5. filtrationThe reaction mixture was filtered
  6. customevaporated under a gentle stream of nitrogen

Sources & evidence

ORD record
ord-1d489020ff774a0087a81308229d10d8
Source dataset
uspto-grants-2001_04
Patent number
US06218542B1

Reaction notes

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