Sodium Carbonate → HCID 68455289, compound

HRID 2357558Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH3:18])=[CH:9][CH:10]=2)[CH:5]=[N:4][N:3]=1.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([CH:26]2[CH2:31][O:30][CH2:29][CH2:28][NH:27]2)=[CH:22][CH:21]=1.C(N(C(C)C)CC)(C)C.C([O-])([O-])=O.[Na+].[Na+]>CN1C(=O)CCC1>[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([CH:26]2[N:27]([C:2]3[C:11]4[C:6](=[CH:7][C:8]([C:12]5[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=5[CH3:18])=[CH:9][CH:10]=4)[CH:5]=[N:4][N:3]=3)[CH2:28][CH2:29][O:30][CH2:31]2)=[CH:24][CH:25]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A solution of 1-chloro-6-o-tolylphthalazine (0.100 g, 0.393 mmol) in NMP (2 mL) was treated with 3-(4-chlorophenyl)morpholine (0.155 g, 0.785 mmol) and diisopropylethylamine (0.219 mL, 1.26 mmol). The reaction solution was stirred at 120° C. in a sealed tube for 16 hours. After cooling to RT, the reaction solution was treated with saturated aqueous Na2CO3 (50 mL). The mixture was extracted with ethyl acetate (3×60 mL) and the combined organic phases were washed with brine. The organic solution was dried over magnesium sulfate and concentrated under reduced pressure. Flash chromatography on silica gel (ethyl acetate) gave 1-(3-(4-chlorophenyl)morpholino)-6-o-tolylphthalazine as a yellow solid. MS (ESI, pos.ion) m/z: 416.1 (M+1).

Workup

temperatureAfter cooling to RT
extractionThe mixture was extracted with ethyl acetate (3×60 mL)
washthe combined organic phases were washed with brine
dry with materialThe organic solution was dried over magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-a89f05c601a047ce8baed3155b936196
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07759337B2

Reaction notes

Loading…