Benzyl Bromide → tert-Butyl 4-(4-(2-(benzyloxy)-5-chlorophenyl)pyridin-2-yl)piperazine-1-carboxylate

HRID 1619717Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:27])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([N:14]3[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]3)[CH:9]=2)[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:34](Br)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>CN(C)C=O>[CH2:34]([O:27][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][C:6]=1[C:8]1[CH:13]=[CH:12][N:11]=[C:10]([N:14]2[CH2:15][CH2:16][N:17]([C:20]([O:22][C:23]([CH3:24])([CH3:26])[CH3:25])=[O:21])[CH2:18][CH2:19]2)[CH:9]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

Conditions

Temperature: 60 °C

Procedure

tert-Butyl 4-(4-(5-chloro-2-hydroxyphenyl)pyridin-2-yl)piperazine-1-carboxylate (Preparation 117, 1.85 g, 4.755 mmol) was dissolved in dimethylformamide (10 mL) at room temperature under a nitrogen atmosphere. Potassium carbonate (1.31 g, 9.51 mmol) was added and the mixture was stirred for 10 minutes. Benzyl bromide (0.622 mL, 5.23 mmol) was added dropwise and the reaction mixture was heated at 60° C. for 18 hours and then partitioned between ethyl acetate (40 mL) and water (20 mL). The organic layer was separated and washed with brine (20 mL), dried over anhydrous MgSO4, filtered and concentrated in vacuo to give the title compound (2.20 g, 96%) as a light yellow solid.

Workup

custompartitioned between ethyl acetate (40 mL) and water (20 mL)
customThe organic layer was separated
washwashed with brine (20 mL)
dry with materialdried over anhydrous MgSO4
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-2a46c29a091e49ff9c2d4a3645b6e408
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772293B2

Reaction notes

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