Methylamine → 2-{[4-(Trifluoromethyl)pyridin-2-yl]methyl}cyclopentan-1-amine

HRID 1750474Notes

Reaction equation

HRID 1750474 reaction equation
CN.[F:3][C:4]([F:29])([F:28])[C:5]1[CH:10]=[CH:9][N:8]=[C:7]([CH2:11][CH:12]2[CH2:16][CH2:15][CH2:14][CH:13]2[N:17]2C(=O)C3C(=CC=CC=3)C2=O)[CH:6]=1>C(O)C>[F:29][C:4]([F:3])([F:28])[C:5]1[CH:10]=[CH:9][N:8]=[C:7]([CH2:11][CH:12]2[CH2:16][CH2:15][CH2:14][CH:13]2[NH2:17])[CH:6]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 1183081562-(2-{[4-(Trifluoromethyl)pyridin-2-yl]methyl}cyclopentyl)-2,3-dihydro-1H-isoindole-1,3-dione

Product 1

HCID 1183082032-{[4-(Trifluoromethyl)pyridin-2-yl]methyl}cyclopentan-1-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methanamine (40% aq, 1 ml, 11.55 mmol) was added to a solution of 2-(2-{[4-(trifluoromethyl)pyridin-2-yl]methyl}cyclopentyl)-2,3-dihydro-1H-isoindole-1,3-dione (0.100 g, 0.27 mmol) in ethanol (6 ml) in a microwave vial. The vial was sealed and stirred at room temperature for 18 hours and then heated to 60° C. for 5 hours. The reaction was cooled to room temperature and concentrated in vacuo. This was then purified by SCX chromatography (2M ammonia in methanol) to afford the title compound.

Workup

  1. customThe vial was sealed
  2. temperatureheated to 60° C. for 5 hours
  3. temperatureThe reaction was cooled to room temperature
  4. concentrationconcentrated in vacuo
  5. customThis was then purified by SCX chromatography (2M ammonia in methanol)

Sources & evidence

ORD record
ord-9f54ff4384a940ef97b0da3a0b9075b3
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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