HCID 178419149, compound → HCID 4025213, compound

HRID 1269375Notes

Reaction equation

HRID 1269375 reaction equation
[C:1]1([N:7]2[CH2:12][CH2:11][N:10]([CH2:13][C:14]3[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.B>CO>[C:1]1([N:7]2[CH2:8][CH2:9][N:10]([CH2:13][C:14]3[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=3)[CH2:11][CH2:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 1

HCID 178419149HCID 178419149, compound

Product 1

HCID 4025213HCID 4025213, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

3-((4-phenyl)piperazin-1-yl)methylpyridine-borane 5 (200 mg, 0.749 mmol) was added to 20 mL of methanol at about 20° C. After complete dissolution, PdO (4.6 mg, 0.037 mmol) was added, and the reaction mixture aged for eight hours at 20–25° C. Palladium black was removed by filtration followed by vacuum concentration of the filtrate to remove methanol and trimethoxyborane. The resulting viscous oil was dissolved in hot hexanes and crystallized by slow cooling to 20° C. The product was washed with cold hexane and dried under vacuum. The yield of 6 was 97% with 100% purity, as determined by HPLC conducted using the system described in Example 1.

Workup

  1. additionwas added
  2. customPalladium black was removed by filtration
  3. customto remove methanol and trimethoxyborane
  4. dissolutionThe resulting viscous oil was dissolved in hot hexanes
  5. customcrystallized
  6. washThe product was washed with cold hexane
  7. customdried under vacuum

Sources & evidence

ORD record
ord-ba2e066f4c8143959f5b83d731913c00
Source dataset
uspto-grants-2007_04
Patent number
US07199240B2

Reaction notes

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