Nanofin → [6-(2,6-Dimethyl-piperidin-1-ylmethyl)-pyridin-2-yl]-carbamic acid tert-butyl ester

HRID 460196

Reaction equation

[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH:4]([CH3:8])[NH:3]1.[C:9]([O:13][C:14](=[O:24])[NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22]Br)[N:17]=1)([CH3:12])([CH3:11])[CH3:10]>CN(C=O)C>[C:9]([O:13][C:14](=[O:24])[NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][N:3]2[CH:4]([CH3:8])[CH2:5][CH2:6][CH2:7][CH:2]2[CH3:1])[N:17]=1)([CH3:12])([CH3:11])[CH3:10]

Participants

Conditions

Temperature: 50 °C

Procedure

2,6-Dimethylpiperidine (0.24 mL, 1.74 mmol) was added to a solution of (6-bromomethyl-pyridin-2-yl)-carbamic acid tert-butyl ester (250 mg, 0.87 mmol) in DMF (10 mL) followed by heating at 50° C. and the resulting mixture was stirred for 18 h. The resulting mixture was partitioned between water (10 mL) and CHCl3 (20 mL). The organic layer was washed with H3O, brine, and dried over MgSO4. Concentration in vacuo gave a pale yellow solid. MS m/z: 320.3 (M+H). Calc'd. for C18H29N3O2-319.23.

Workup

customThe resulting mixture was partitioned between water (10 mL) and CHCl3 (20 mL)
washThe organic layer was washed with H3O, brine
dry with materialdried over MgSO4
concentrationConcentration in vacuo
customgave a pale yellow solid

Sources & evidence

ORD record: ord-3fc3ef085f324258a1fb269005bd6d96
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07196104B2

Linked notes

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