Water → HCID 58792696, compound

HRID 1365089Notes

Reaction equation

Cl[CH2:2][C:3]([NH:5][C:6]1[CH:7]=[CH:8][C:9]2[C:10](=[O:19])[C:11]3[C:16]([C:17]=2[CH:18]=1)=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:4].C([O-])([O-])=O.[K+].[K+].O.[C:27]([O:30][CH2:31]C)(=[O:29])[CH3:28].C[N:34]([CH:36]=O)[CH3:35]>>[CH3:31][O:30][C:27](=[O:29])[C:28]1[CH:17]=[CH:9][CH:8]=[CH:7][C:36]=1[NH:34][CH:35]1[CH2:18][CH2:6][N:5]([CH2:2][C:3](=[O:4])[NH:5][C:6]2[CH:7]=[CH:8][C:9]3[C:10](=[O:19])[C:11]4[C:16]([C:17]=3[CH:18]=2)=[CH:15][CH:14]=[CH:13][CH:12]=4)[CH2:3][CH2:2]1

Participants

Reactant 5

HCID 962Water

HCID 6228Dimethylformamide

HCID 8857Ethyl Acetate

HCID 11430Potassium Carbonate

HCID 114486452-Chloro-N-(9-oxo-9H-fluoren-3-yl)-acetamide

Product 1

HCID 58792696HCID 58792696, compoundYield 77%

Conditions

Temperature: 10 °C

Procedure

A mixture of 2-(Piperidine-4-yl-amino)-methyl benzoate (1100 mg, 4.70 mmol), 2-Chloro-N-(9-oxo-9H-fluoren-3-yl)-acetamide (1358 mg, 5 mmol) and K2CO3 (1380 mg, 10 mmol) in DMF (40 mL) was stirred at 10° C. for 2 hours and then at room temperature overnight. The reaction mixture was added to 50 mL water and 100 mL ethyl acetate, the organic phase was decanted and washed with water (3×50 mL), dried over sodium sulfate and a 2.8 M hydrogen chloride solution in absolute ethanol (1.80 mL) was added, to precipitate the hydrochloride, which was filtered off and washed with ethyl acetate. 1840 mg of a white solid were obtained. Yield: 77%.

Workup

customat room temperature
customovernight
customthe organic phase was decanted
washwashed with water (3×50 mL)
dry with materialdried over sodium sulfate
additiona 2.8 M hydrogen chloride solution in absolute ethanol (1.80 mL) was added
customto precipitate the hydrochloride, which
filtrationwas filtered off
washwashed with ethyl acetate

Sources & evidence

ORD record: ord-de5906374a9d403e8d8892522d3b5894
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07888510B2

Reaction notes

Loading…