Methylamine → HCID 59295980, compound
Reaction equation
F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)[N:10]1CCC[CH2:11]1.[C:25]([O:29][C:30]([N:32]1[CH2:37][CH2:36][CH:35]([O:38][C:39]2[CH:47]=[CH:46][C:45]([Cl:48])=[CH:44][C:40]=2[C:41](O)=[O:42])[CH2:34][CH2:33]1)=[O:31])([CH3:28])([CH3:27])[CH3:26].CN>C(Cl)Cl>[C:25]([O:29][C:30]([N:32]1[CH2:37][CH2:36][CH:35]([O:38][C:39]2[CH:47]=[CH:46][C:45]([Cl:48])=[CH:44][C:40]=2[C:41](=[O:42])[NH:10][CH3:11])[CH2:34][CH2:33]1)=[O:31])([CH3:28])([CH3:27])[CH3:26]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Bromo-tris-pyrrolidinophosphonium hexafluorophosphate (1.57 g, 3.37 mmol) was added to a vigorously stirred mixture of 2-{[1-(tert-butoxycarbonyl)piperidin-4-yl]oxy}-5-chlorobenzoic acid (1.00 g, 2.8 mmol) and 40% aq methylamine (2 ml) in DCM (10 ml). Stirring was continued for 30 min. before partitioning between 1N hydrochloric acid (10 ml) and dichloromethane (10 ml). The organic layer was separated and washed with saturated sodium bicarbonate solution (20 ml) and water (20 ml), then dried over sodium sulfate and the solvent removed under reduced pressure. The residue was purified by flash column chromatography eluting with ethyl acetate:isohexane (1:1) to give the title compound as a colourless solid (0.84 g).
Workup
- custombefore partitioning between 1N hydrochloric acid (10 ml) and dichloromethane (10 ml)
- customThe organic layer was separated
- washwashed with saturated sodium bicarbonate solution (20 ml) and water (20 ml)
- dry with materialdried over sodium sulfate
- customthe solvent removed under reduced pressure
- customThe residue was purified by flash column chromatography
- washeluting with ethyl acetate:isohexane (1:1)
Sources & evidence
- ORD record
- ord-5498d88283d34f37bddf0f994e50dd41
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07709500B2
Reaction notes
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