Thiophene → 1-[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-N-[(4-fluorophenyl)methyl]-4-piperidinemethanamine

HRID 579797Notes

Reaction equation

HRID 579797 reaction equation
Br.Br.[O:3]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[O:6][CH2:5][CH:4]1[CH2:13][N:14]1[CH2:19][CH2:18][CH:17]([CH2:20][NH2:21])[CH2:16][CH2:15]1.[F:22][C:23]1[CH:30]=[CH:29][C:26]([CH:27]=O)=[CH:25][CH:24]=1.S1C=CC=C1.[O-2].[Ca+2].[H][H]>CO.[Pd]>[O:3]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[O:6][CH2:5][CH:4]1[CH2:13][N:14]1[CH2:15][CH2:16][CH:17]([CH2:20][NH:21][CH2:27][C:26]2[CH:29]=[CH:30][C:23]([F:22])=[CH:24][CH:25]=2)[CH2:18][CH2:19]1

Participants

8

Reactant 5

HCID 8030ThiopheneHCID 680234-FluorobenzaldehydeHCID 6850728CalciumoxideHCID 140490391-[(2,3-Dihydro-1,4-benzodioxin-2-yl)methyl]-4-piperidinemethanamine dihydrobromideHCID 178418361HCID 178418361, compound

Product 1

HCID 212416171-[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-N-[(4-fluorophenyl)methyl]-4-piperidinemethanamineYield 98.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A mixture of 5 parts of 1-[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-4piperidinemethanamine dihydrobromide, 1.6 parts of 4-fluorobenzaldehyde, 3 parts of a solution of thiophene in methanol 4%, 200 parts of methanol and 4 parts of calcium oxide 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, yielding 4.3 parts (98.3%) of 1-[(2,3-dihydro-1,4-benzodioxin-2-yl)-methyl]-N-[(4-fluorophenyl)methyl]-4-piperidinemethanamine as an oily residue (intermediate 82).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-5a6ba7b128fd4314869285f30ab2fa17
Source dataset
uspto-grants-1988_06
Patent number
US04749702

Reaction notes

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