Triethylamine → 1-Diazo-3-(3,4-dichlorophenyl)-5-(4-hydroxy-4-phenyl-1-piperidinyl)-2-pentanone

HRID 357247Notes

Reaction equation

HRID 357247 reaction equation
Br[CH2:2][CH2:3][CH:4]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([Cl:17])[CH:11]=1)[C:5](=[O:9])[CH:6]=[N+:7]=[N-:8].CC[N:20]([CH2:23][CH3:24])[CH2:21][CH3:22].CCO[C:28]([CH3:30])=[O:29]>>[N+:7](=[CH:6][C:5](=[O:9])[CH:4]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([Cl:17])[CH:11]=1)[CH2:3][CH2:2][N:20]1[CH2:21][CH2:22][C:28]([OH:29])([C:30]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:24][CH2:23]1)=[N-:8]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 537812765-Bromo-1-diazo-3-(3,4-dichlorophenyl)-2-pentanone

Product 1

HCID 539157251-Diazo-3-(3,4-dichlorophenyl)-5-(4-hydroxy-4-phenyl-1-piperidinyl)-2-pentanone

Procedure

Dissolve the product of Step 4 (3.93 g, 11.7 mmoles) in 50 ml of dry EtOAc. Add 4-hydroxy-4-phenyl-1-piperidine (2.55 g, 14.4 mmoles), followed by dry Et3N (13.3 ml.). Heat under N2 at 60°-65° C. for 28 h. Cool to room temperature, filter the solid and wash with EtOAc. Apply the filtrate 1 5 to a silica gel column and elute the column with 1.5% CH3OH(NH3)/EtOAc. Yield: 2.34 g; Cl-MS: m/e=432 (M+H+, 35Cl+37Cl isotope).

Workup

  1. temperatureHeat under N2 at 60°-65° C. for 28 h
  2. filtrationfilter the solid
  3. washwash with EtOAc
  4. washApply the filtrate 1 5 to a silica gel column and elute the column with 1.5% CH3OH(NH3)/EtOAc

Sources & evidence

ORD record
ord-6487fd7f66324a05b5df4c52a043a36b
Source dataset
uspto-grants-1998_11
Patent number
US05840725

Reaction notes

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