Potassium Hydroxide → HCID 86619155, compound

HRID 1060185Notes

Reaction equation

HRID 1060185 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C@H:10]2[CH2:15][C@H:14]([N:16]3[CH2:21][CH2:20][N:19]([CH2:22][C:23]([NH:25][C:26]4[C:31]([CH3:32])=[CH:30][CH:29]=[CH:28][C:27]=4[CH3:33])=[O:24])[CH2:18][CH2:17]3)[CH2:13][CH2:12][N:11]2C(OCC)=O)[CH:5]=[CH:6][C:7]=1[Cl:8].[OH-].[K+]>CC(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C@H:10]2[CH2:15][C@H:14]([N:16]3[CH2:21][CH2:20][N:19]([CH2:22][C:23]([NH:25][C:26]4[C:27]([CH3:33])=[CH:28][CH:29]=[CH:30][C:31]=4[CH3:32])=[O:24])[CH2:18][CH2:17]3)[CH2:13][CH2:12][NH:11]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 86619156HCID 86619156, compound

Product 1

HCID 86619155HCID 86619155, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of intermediate 11 (0.0034 mol) and potassium hydroxide (0.034 mol) in 2-propanol (150 ml) was stirred and refluxed for 4 days. The solvent was evaporated. The residue was taken up in CH2Cl2/water. The organic layer was separated, dried, filtered and the solvent was evaporated. The residue was purified by column chromato-graphy over silica gel (eluent: CH2Cl2/(CH3OH/NH3) 95/5). The pure fractions were collected and the solvent was evaporated, yielding 0.5 g (30%) of (±)-trans-4-[2-[(3,4-dichlorophenyl)methyl]-4-piperidinyl]-N-(2,6-dimethylphenyl)-1-piperazineacetamide (intermediate 13).

Workup

  1. temperaturerefluxed for 4 days
  2. customThe solvent was evaporated
  3. customThe organic layer was separated
  4. customdried
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. customThe residue was purified by column chromato-graphy over silica gel (eluent: CH2Cl2/(CH3OH/NH3) 95/5)
  8. customThe pure fractions were collected
  9. customthe solvent was evaporated

Sources & evidence

ORD record
ord-0e79153b0773417f9eab00cbdc194cdd
Source dataset
uspto-grants-2003_02
Patent number
US06521621B1

Reaction notes

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