1-Pyrrolidineethanamine → HCID 57639973, compound
Reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[C:4]([O:11][CH3:12])[CH:3]=1.[N:13]1([CH2:18][CH2:19][NH2:20])[CH2:17][CH2:16][CH2:15][CH2:14]1.CCN(C(C)C)C(C)C>CC(N(C)C)=O>[CH3:12][O:11][C:4]1[CH:3]=[C:2]([NH:20][CH2:19][CH2:18][N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[CH:7]=[CH:6][C:5]=1[NH2:8]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a stirred solution of 4-fluoro-2-methoxy-1-nitro-benzene (Fluorochem; 2.57 g; 15 mmol) in DMA was 2-pyrrolidin-1-ylethanamine (Aldrich; 1.88 g, 16.5 mmol) followed by DIPEA (2.97 mL, 18 mmol). The mixture was heated at 80° C. for 20 hours, then cooled to room temp. The mixture was concentrated in vacuo, dissolved in DCM and purified by SCX (50 g SCX 2 column). The product was eluted from the column with 7N ammonia in methanol, concentrated in vacuo to give the title compound (53 mg) which was dissolved in Methanol as a 0.05 mmol solution and reduced using an H-cube hydrogenator. 10% Pd/C catalyst, 1 bar hydrogen (full hydrogen setting), 3 mL/min flow-rate at 50° C. The resultant solution was concentrated in vacuo, and the resultant material purified by column chromatography, eluting with 0-10% ammonia/methanol in DCM, to give the title compound as a solid.
Workup
- temperaturecooled to room temp
- concentrationThe mixture was concentrated in vacuo
- dissolutiondissolved in DCM
- custompurified by SCX (50 g SCX 2 column)
- washThe product was eluted from the column with 7N ammonia in methanol
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-5dcf8aeb8608405b975063335e78be7d
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07709471B2
Reaction notes
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