Methyl Ethyl Ketone → HCID 70047987, compound

HRID 1419941Notes

Reaction equation

HRID 1419941 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.[CH2:22]([C:29]1([OH:35])[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+].CC(=O)CC>O>[CH2:22]([C:29]1([OH:35])[CH2:34][CH2:33][N:32]([CH2:18][CH2:17][CH2:16][NH:15][C:13](=[O:14])[C:12]2[CH:20]=[CH:21][C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:10][CH:11]=2)[CH2:31][CH2:30]1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 981524-Benzyl-4-piperidinolHCID 54365031HCID 54365031, compound

Product 1

HCID 70047987HCID 70047987, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-benzyloxy-N-(3-chloro-propyl)-benzamide (0.5 g, 1.64 mmol), ), 4-benzyl-4-hydroxy-piperidine (0.315 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 N-[3-(4-benzyl-4-hydroxy-piperidin-1-yl)-propyl]-4-benzyloxy-benzamide (185 mg, 25%) as a light yellow solid. MS: me/e=459 (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-52ae52feeb54407b9f2f12141901e010
Source dataset
uspto-grants-1999_03
Patent number
US05889026

Reaction notes

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