Cyclohexylamine → HCID 53628955, compound
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]2[CH:19]=[CH:18][C:17](Br)=[CH:16][CH:15]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.CC(C)([O-])C.[Na+].[CH:48]1([NH2:54])[CH2:53][CH2:52][CH2:51][CH2:50][CH2:49]1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]2[CH:19]=[CH:18][C:17]([NH:54][CH:48]3[CH2:53][CH2:52][CH2:51][CH2:50][CH2:49]3)=[CH:16][CH:15]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 90 °C
Procedure
To a suspension of 3-(4-bromophenyl)-piperidine-1-carboxylic acid tert-butyl ester (8.0 g, 23.5 mmol), palladium acetate (210 mg, 0.94 mmol), 2-(di-t-butyl phosphino)biphenyl (560 mg, 1.88 mmol), and sodium t-butoxide (3.2 g, 33.3 mmol) in toluene (80 mL) was added cyclohexylamine (2.8 g, 28.2 mmol) at room temperature. After heating at 90° C. for 5 h, the resulting suspension was passed through a Celite column. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel chromatography eluting 5-25% of ethyl acetate in hexane to afford 3-(4-cyclohexylaminophenyl)-piperidine-1-carboxylic acid tert-butyl ester (6.74 g, 18.8 mmol, 80%) as white crystals.
Workup
- concentrationThe filtrate was concentrated under reduced pressure
- customthe residue was purified by silica gel chromatography
- washeluting 5-25% of ethyl acetate in hexane
Sources & evidence
- ORD record
- ord-3969d37275cb4f06a9a9b44160e37bd3
- Source dataset
- uspto-grants-2009_03
- Patent number
- US07504411B2
Reaction notes
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