Benzyl chloroformate → HCID 67264982, compound

HRID 1685156Notes

Reaction equation

HRID 1685156 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[N:15]([CH2:27][CH2:28][N:29](CC3C=CC=CC=3)[CH3:30])[CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[C:21]([F:26])[CH:20]=3)[N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:39]([O:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)=[O:40]>C(#N)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[N:15]([CH2:27][CH2:28][N:29]([C:39]([O:41][CH2:42][C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)=[O:40])[CH3:30])[CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[C:21]([F:26])[CH:20]=3)[N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 67264986HCID 67264986, compound

Product 1

HCID 67264982HCID 67264982, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Charge 4-[1-[2-(benzyl-methyl-amino)-ethyl]-4-(3,4-difluoro-phenyl)-1H-imidazol-2-yl]-piperidine-1-carboxylic acid tert-butyl ester (1.8 g; 0.0035 mol; 1.0 equiv) in ACN (40 mL) under nitrogen and add benzyl chloroformate drop wise at 0° C. Stir the reaction for 30 min and bring to RT. Stir at RT for 1.5 h. After completion, quench the reaction with saturated sodium bicarbonate solution and extract in EA. Wash with water and brine, dry over anhydrous sodium sulfate and evaporate off the solvent under vacuum. Purify on silica column using 15% EA/hexane to get the title compound (1.6 g; 82%). (ES+): m/z=555 (M+H).

Workup

  1. customdrop wise at 0° C
  2. customthe reaction for 30 min
  3. custombring to RT
  4. stirringStir at RT for 1.5 h
  5. customAfter completion, quench
  6. customthe reaction with saturated sodium bicarbonate solution
  7. extractionextract in EA
  8. washWash with water and brine
  9. dry with materialdry over anhydrous sodium sulfate
  10. customevaporate off the solvent under vacuum
  11. customPurify on silica column

Sources & evidence

ORD record
ord-2b92eab79e3845f49180b24344b20ae4
Source dataset
uspto-grants-2012_04
Patent number
US08148387B2

Reaction notes

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