Methyl Ethyl Ketone → HCID 70047982, compound

HRID 1419938Notes

Reaction equation

HRID 1419938 reaction equation
[CH2:1]([O:8][C:9]1[CH:20]=[CH:19][C:12]([C:13]([NH:15][CH2:16][CH2:17]Cl)=[O:14])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:21]([C:28]1([OH:34])[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[C:35](=O)([O-])[O-].[K+].[K+].CC(=O)CC>O>[CH2:1]([O:8][C:9]1[CH:20]=[CH:19][C:12]([C:13]([NH:15][CH2:16][CH2:17][N:31]2[CH2:32][CH2:33][C:28]([OH:34])([CH2:21][C:22]3[CH:23]=[CH:24][C:25]([CH3:35])=[CH:26][CH:27]=3)[CH2:29][CH2:30]2)=[O:14])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 981524-Benzyl-4-piperidinolHCID 54388472HCID 54388472, compound

Product 1

HCID 70047982HCID 70047982, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-benzyloxy-N-(2-chloro-ethyl)-benzamide (2.1 g, 7.25 mmol), 4-benzyl-4-hydroxy-piperidine (1.386 g, 7.25 mmol), potassium carbonate (2.0 g, 14.5 mmol) and 2-butanone (40 ml) was stirred for 15 h at 60° C. After the addition of water, the mixture was extracted with ethyl acetate. The organic layer was dried (Na2SO4), filtered and evaporated. The residue was purified by chromatography (silica gel, methylene chloride methanol from 95:5 to 9:1) to give 4-benzyloxy-N-[2-[4-hydroxy-4-(4-methyl-benzyl)-piperidin-1-yl]-ethyl]-benzamide (680 mg, 21%) as a light yellow solid. MS: me/e=445 (M+H)+.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by chromatography (silica gel, methylene chloride methanol from 95:5 to 9:1)

Sources & evidence

ORD record
ord-78d933658fe44eda87502ae8d596d262
Source dataset
uspto-grants-1999_03
Patent number
US05889026

Reaction notes

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