Potassium Carbonate → 9-[4-(3-Pyrrolidin-1-yl-propoxy)-phenyl]-1,2,3,4-tetrahydro-acridine

HRID 2251101Notes

Reaction equation

[CH2:1]1[C:14]2[C:5](=[N:6][C:7]3[C:12]([C:13]=2[C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH2:4][CH2:3][CH2:2]1.Cl[CH2:23][CH2:24][CH2:25][N:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1.C([O-])([O-])=O.[K+].[K+]>CN1C(=O)CCC1>[N:26]1([CH2:25][CH2:24][CH2:23][O:21][C:18]2[CH:19]=[CH:20][C:15]([C:13]3[C:12]4[C:7]([N:6]=[C:5]5[C:14]=3[CH2:1][CH2:2][CH2:3][CH2:4]5)=[CH:8][CH:9]=[CH:10][CH:11]=4)=[CH:16][CH:17]=2)[CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

Conditions

Temperature: 80 °C

Procedure

The product from the previous step, 4-(1,2,3,4-Tetrahydro-acridin-9-yl)-phenol (22 mg, 0.08 mmol), 1-(3-Chloropropyl)-pyrrolidine (18 mg, 0.12 mmol), and K2CO3 (17 mg, 0.12 mmol) were mixed in NMP (267 uL) and stirred rapidly at 80° C. for 90 minutes in a sealed vial. The reaction mixture was cooled, partitioned between Et2O (50 mL) and H2O (10 mL). The organic layer was washed with H2O (3×10 mL), sat. aq. NaCl (10 mL), dried over Na2SO4, decanted and concentrated. The residue was purified using preparative LCMS to give product the desired product.

Workup

temperatureThe reaction mixture was cooled
custompartitioned between Et2O (50 mL) and H2O (10 mL)
washThe organic layer was washed with H2O (3×10 mL), sat. aq. NaCl (10 mL)
dry with materialdried over Na2SO4
customdecanted
concentrationconcentrated
customThe residue was purified

Sources & evidence

ORD record: ord-f2a3fe71566e47c0bd2b0e32fcc1ca25
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07319103B2

Reaction notes

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