Sodium Carbonate → 1-Propanone, 1-[4-(phenylamino)-1-[2-(2-thienyl)ethyl]-4-piperidinyl]-

HRID 1973798Notes

Reaction equation

HRID 1973798 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7]O.[C:9]1([NH:15][C:16]2([C:22](=[O:25])[CH2:23][CH3:24])[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[Na+].[Na+]>CC(C)CC(=O)C>[C:9]1([NH:15][C:16]2([C:22](=[O:25])[CH2:23][CH3:24])[CH2:21][CH2:20][N:19]([CH2:7][CH2:6][C:2]3[S:1][CH:5]=[CH:4][CH:3]=3)[CH2:18][CH2:17]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 794002-ThiopheneethanolHCID 122982271-Propanone, 1-[4-(phenylamino)-4-piperidinyl]-

Product 1

HCID 122982231-Propanone, 1-[4-(phenylamino)-1-[2-(2-thienyl)ethyl]-4-piperidinyl]-

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 4.1 parts of 2-thiopheneethanol, methanesulfonate ester, 3.5 parts of 1-[4-(phenylamino)-4-piperidinyl]-1-propanone, 5.3 parts of sodium carbonate and 120 parts of 4-methyl-2-pentanone is stirred and refluxed for 18 hours. After cooling to room temperature, the reaction mixture is poured onto water and the layers are separated. The organic phase is dried, filtered and evaporated. The oily residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and 5% of methanol as eluent. The pure fractions are collected and the eluent is evaporated. The solid residue is crystallized from 2,2'-oxybispropane. The product is filtered off and dried, yielding 1-{4-(phenylamino)-1-[2-(2-thienyl)ethyl]-4-piperidinyl}-1-propanone; mp. 127.1° C.

Workup

  1. temperaturerefluxed for 18 hours
  2. additionthe reaction mixture is poured onto water
  3. customthe layers are separated
  4. customThe organic phase is dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe oily residue is purified by column-chromatography over silica gel using
  8. additiona mixture of trichloromethane and 5% of methanol as eluent
  9. customThe pure fractions are collected
  10. customthe eluent is evaporated
  11. customThe solid residue is crystallized from 2,2'-oxybispropane
  12. filtrationThe product is filtered off
  13. customdried

Sources & evidence

ORD record
ord-dc85c121f1e64873b71c664d6ef53b8d
Source dataset
uspto-grants-1976_12
Patent number
US03998834

Reaction notes

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