Methyl Ethyl Ketone → HCID 70045694, compound

HRID 1419942Notes

Reaction equation

HRID 1419942 reaction equation
[CH2:1]([O:8][C:9]1[CH:21]=[CH:20][C:12]([C:13]([NH:15][CH2:16][CH2:17][CH2:18]Cl)=[O:14])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:22][C:23]1([CH2:29][C:30]2[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=2)[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.C(=O)([O-])[O-].[K+].[K+].CC(=O)CC>O>[CH2:1]([O:8][C:9]1[CH:21]=[CH:20][C:12]([C:13]([NH:15][CH2:16][CH2:17][CH2:18][N:26]2[CH2:27][CH2:28][C:23]([OH:22])([CH2:29][C:30]3[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=3)[CH2:24][CH2:25]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 105362424-(4-Methylbenzyl)-piperidin-4-olHCID 54365031HCID 54365031, compound

Product 1

HCID 70045694HCID 70045694, compoundYield 28.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-benzyloxy-N-(3-chloro-propyl)-benzamide (0.5 g, 1.64 mmol), ), 4-hydroxy-4-(4-methyl-benzyl)-piperidine (0.34 g, 1.65 mmol), potassium carbonate (0.45 g, 3.29 mmol) and 2-butanone (10 ml) was stirred at 60° C. for 48 h. 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-[3-[4-hydroxy-4-(4-methyl-benzyl)-piperidin-1-yl]-propyl]-benzamide (220 mg, 28%) as light yellow solid. MS: me/e =473 (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-7c49a28f6c4e4f3e92e76d205d68456c
Source dataset
uspto-grants-1999_03
Patent number
US05889026

Reaction notes

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