Potassium Carbonate → Tert-butyl 4-(2-(3,3-diphenylpropylamino)ethyl)piperidine-1-carboxylate

HRID 2190297Notes

Reaction equation

Br[CH2:2][CH2:3][CH:4]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[NH2:17][CH2:18][CH2:19][CH:20]1[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:5]1([CH:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:3][CH2:2][NH:17][CH2:18][CH2:19][CH:20]2[CH2:21][CH2:22][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:24][CH2:25]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

Conditions

Temperature: 65 °C

Procedure

3-bromo-1,1-diphenylpropane (2.6 g, 9 mmol) and tert-butyl 4-(2-aminoethyl)piperidine-1-carboxylate (4.7 g, 21 mmol) were mixed together in acetonitrile (100 ml) and potassium carbonate (1.3 g, 9 mmol) was added. The resulting mixture was heated to 65° C. with stirring under N2 overnight. After that time the mixture was cooled and concentrated under reduced pressure. The residue was partitioned between DCM and water. The DCM layer was washed with water, dried over MgSO4 and concentrated under reduced pressure to give the crude product as a clear oil. The crude product was purified by combiflash (0-10% MeOH/DCM) to give tert-butyl 4-(2-(3,3-diphenylpropylamino)ethyl)piperidine-1-carboxylate 48

Workup

temperatureAfter that time the mixture was cooled
concentrationconcentrated under reduced pressure
customThe residue was partitioned between DCM and water
washThe DCM layer was washed with water
dry with materialdried over MgSO4
concentrationconcentrated under reduced pressure
customto give the crude product as a clear oil
customThe crude product was purified by combiflash (0-10% MeOH/DCM)

Sources & evidence

ORD record: ord-af392d7a01494aa1af414039b10d11c3
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324396B2

Reaction notes

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