Ammonia → HCID 68939390, compound

HRID 272530Notes

Reaction equation

HRID 272530 reaction equation
Cl[C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([CH:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)[CH2:10][CH2:9]2)[CH:5]=[CH:4][N:3]=1.[NH3:19]>CO.[Cu]>[CH:14]1([N:11]2[CH2:12][CH2:13][N:8]([C:6]3[CH:5]=[CH:4][N:3]=[C:2]([NH2:19])[CH:7]=3)[CH2:9][CH2:10]2)[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 86605572HCID 86605572, compound

Product 1

HCID 68939390HCID 68939390, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 887MethanolSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 5.84 g (22 mmol) 1-(2-chloro-pyridin-4-yl)-4-cyclopentyl-piperazine, 0.8 g copper powder in 41 ml 7M ammonia in methanol was heated to 150° C. for 18 h. After evaporation to dryness the residue was purified on silica eluting with a gradient formed from dichloromethane/methanol and NEt3. The evaporation of the combined product fractions yielded 1.29 g (24%) of the title compound as yellowish solid. (m/e): 247.3 (MH+; 100%).

Workup

  1. customAfter evaporation to dryness the residue
  2. customwas purified on silica eluting with a gradient
  3. customformed from dichloromethane/methanol and NEt3
  4. customThe evaporation of the combined product fractions

Sources & evidence

ORD record
ord-45a4b13acfe4471693e0d6b566c52c16
Source dataset
uspto-grants-2008_11
Patent number
US07456175B2

Reaction notes

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