Methyl Isobutyl Ketone → HCID 20185173, compound

HRID 2309632Notes

Reaction equation

HRID 2309632 reaction equation
[ClH:1].Cl.[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[C:15]3=[N:16][CH:17]=[CH:18][CH:19]=[C:14]3[N:13]=[C:12]2[CH2:20][CH:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)=[CH:6][CH:5]=1.C(=O)([O-])[O-].[Na+].[Na+].CC(C)CC(=O)C.CS(O[CH2:45][CH2:46][C:47]1[S:48][CH:49]=[CH:50][CH:51]=1)(=O)=O>O>[ClH:1].[ClH:1].[F:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][N:11]2[C:15]3=[N:16][CH:17]=[CH:18][CH:19]=[C:14]3[N:13]=[C:12]2[CH2:20][CH:21]2[CH2:26][CH2:25][N:24]([CH2:45][CH2:46][C:47]3[S:48][CH:49]=[CH:50][CH:51]=3)[CH2:23][CH2:22]2)=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 7909Methyl Isobutyl KetoneHCID 10340Sodium CarbonateHCID 30477232-(2-Thienyl)ethyl methanesulphonateHCID 20037917HCID 20037917, compound

Product 1

HCID 20185173HCID 20185173, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 7.9 parts of 3-[(4-fluorophenylmethyl)-2-(4-piperidinylmethyl)-3H-imidazo[4,5-b]pyridine dihydrochloride, 8.5 parts of sodium carbonate and 120 parts of 4-methyl-2-pentanone was stirred and refluxed for 30 minutes using a water separator. 7.8 Parts of 2-thiopheneethanol methanesulfonate (ester) were added and the whole was stirred and refluxed for 4 hours using a water separator. After cooling, the salts were filtered off, washed with 4-methyl-2-pentanone and the filtrate was washed with water. The organic layer was dried, filtered and evaporated. The residue was converted into the hydrochloride salt in 2-propanol and 2-propanone. The salt was filtered off and dried in vacuo at 60° C., yielding 8.0 parts (76%) of 3-[(4-fluorophenyl)methyl]-2-[[1-[2-(2-thienyl)ethyl]-4-piperidinyl]methyl]-3H-imidazo[4,5-b]pyridine dihydrochloride. monohydrate; mp. 210.8° C. (117).

Workup

  1. temperaturerefluxed for 30 minutes
  2. stirringthe whole was stirred
  3. temperaturerefluxed for 4 hours
  4. temperatureAfter cooling
  5. filtrationthe salts were filtered off
  6. washwashed with 4-methyl-2-pentanone
  7. washthe filtrate was washed with water
  8. customThe organic layer was dried
  9. filtrationfiltered
  10. customevaporated
  11. filtrationThe salt was filtered off
  12. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-6c078029ea124d4387786bbd6a8f70ed
Source dataset
uspto-grants-1987_09
Patent number
US04695575

Reaction notes

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