Benzylamine → HCID 67914544, compound

HRID 345586Notes

Reaction equation

HRID 345586 reaction equation
[CH2:1]([N:3]([CH2:25][CH3:26])[CH2:4][CH2:5][O:6][CH:7]1[C:12](=O)[CH2:11][CH2:10][N:9]([CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH2:8]1)[CH3:2].C1(C[NH2:34])C=CC=CC=1.S1C=CC=C1.[H][H]>C(O)C.[Pd].CO>[CH2:1]([N:3]([CH2:25][CH3:26])[CH2:4][CH2:5][O:6][C@H:7]1[C@@H:12]([NH2:34])[CH2:11][CH2:10][N:9]([CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH2:8]1)[CH3:2]

Participants

8

Reactant 4

HCID 7504BenzylamineHCID 8030ThiopheneHCID 19883507HCID 19883507, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67914544HCID 67914544, compoundYield 45%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A mixture of 8.0 parts of 3-[2-(diethylamino)ethoxy]-1-[3-(4-fluorophenoxy)propyl]-4-piperidinone, 2.5 parts of benzenemethanamine, 1 part of a solution of thiophene in ethanol 4% and 120 parts of methanol was hydrogenated at normal pressure and at room temperature with 2 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated. The residue was purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) saturated with ammonia, as eluent. The pure fractions were collected and the eluent was evaporated, yielding 3.6 parts (45%) of cis-3-[2-(diethlamino)ethoxy]-1-[3-(4-fluorophenoxy)-propyl]-4-piperidinamine as a residue (intermediate 126).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe residue was purified by column-chromatography over silica gel using
  4. additiona mixture of trichloromethane and methanol (95:5 by volume) saturated with ammonia
  5. customThe pure fractions were collected
  6. customthe eluent was evaporated

Sources & evidence

ORD record
ord-fbd04cf69894403ab3a208ff45fc01f4
Source dataset
uspto-grants-1991_10
Patent number
US05057525

Reaction notes

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