Potassium Carbonate → 1-(Benzothiazol-2-yl)-3-(SR)-((4-phenyl)piperidin-1-yl)methyl-4-(SR)-phenylpyrrolidine

HRID 1276504Notes

Reaction equation

[C:1]1([CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH:14]3[CH:18]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH2:17][NH:16][CH2:15]3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:26]1[S:27][C:28]2[CH:34]=[CH:33][CH:32]=[CH:31][C:29]=2[N:30]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[S:27]1[C:28]2[CH:34]=[CH:33][CH:32]=[CH:31][C:29]=2[N:30]=[C:26]1[N:16]1[CH2:17][CH:18]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:14]([CH2:13][N:10]2[CH2:9][CH2:8][CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:12][CH2:11]2)[CH2:15]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 54 mg (0.16 mmol) of 3-(SR)-((4-phenyl)piperidin-1-yl)methyl-4-(SR)-phenylpyrrolidine (from Example 30, Step A), 53 mg (0.31 mmol) of (2-chloro)benzothiazole and 65 mg (0.47 mmol) of K2CO3 in 3 mL of DMF was heated at 80° C. for 1 h. The reaction mixture was cooled, partitioned between 25 mL of ether and 15 mL of H2O and the layers were separated. The organic layer was dried over MgSO4 and concentrated in vacuo. Flash chromatography on 15 g of silica gel using 1:1 v/v hexnaes/EtOAc as the eluant afforded 16 mg (23%) of the title compound as an oil. 1H NMR (500 MHz, CDCl3): δ1.79-3.04 (12H), 3.29 (q, J=8.9, 1H), 3.55 (t, J=9.0, 1H), 3.69 (t, J=9.6, 1H), 4.03-4.11 (m, 2H), 7.07-7.64 (14H). Mass Spectrum (NH3 -CI): 454 (M+.1).

Workup

temperatureThe reaction mixture was cooled
custompartitioned between 25 mL of ether and 15 mL of H2O
customthe layers were separated
dry with materialThe organic layer was dried over MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-4fdfcdad8bc64edead64249682006fc9
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06166037

Reaction notes

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