Water → HCID 53392351, compound

HRID 1922386Notes

Reaction equation

[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][CH2:10][CH2:9]2)[CH2:4][CH2:3]1.C1C(=O)N([Br:25])C(=O)C1.O>CN(C=O)C>[Br:25][C:14]1[CH:13]=[C:12]2[C:17](=[CH:16][CH:15]=1)[N:8]([CH:5]1[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]1)[CH2:9][CH2:10][CH2:11]2

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 1-(1-methylpiperidin-4-yl)-1,2,3,4-tetrahydroquinoline (500 mg, 2.17 mmol) in 7 mL of DMF was cooled to 0° C. then treated dropwise with NBS (386 mg, 2.17 mmol) in 7 mL DMF. The reaction was stirred at 0° C. for 2 hours then treated with 30 mL H2O. The suspension was extracted with 100 mL EtOAc. The organic layer was dried over MgSO4, filtered and concentrated to give a dark residue, which was filtered through a short plug of silica gel using 5%, 2M NH3 in MeOH/CH2Cl2 (100 mL). The filtrate was concentrated and subjected to flash chromatography on silica gel using 5% MeOH/CH2Cl2 then 5% 2M NH3 in MeOH/CH2Cl2. A light yellow oil was obtained (490 mg, 73.0%). 1H-NMR (CDCl3) δ: 7.10 (dd, J=2.1, 10.8 Hz), 7.04-7.03 (m, 1H), 6.50 (d, J=9.0 Hz, 1H), 3.57-3.47 (m, 1H), 3.18 (t, J=5.7 Hz, 2H), 2.98-2.94 (m, 2H), 2.68 (t, J=6.0 Hz, 2H), 2.31 (s, 3H), 2.10-2.02 (m, 2H), 1.91-1.69 (m, 6H).

Workup

extractionThe suspension was extracted with 100 mL EtOAc
dry with materialThe organic layer was dried over MgSO4
filtrationfiltered
concentrationconcentrated
customto give a dark residue, which
filtrationwas filtered through a short plug of silica gel using 5%, 2M NH3 in MeOH/CH2Cl2 (100 mL)
concentrationThe filtrate was concentrated
customA light yellow oil was obtained (490 mg, 73.0%)

Sources & evidence

ORD record: ord-a8d0721122784ca096d8bb817d990564
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08173813B2

Reaction notes

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