Sodium Carbonate → HCID 46947043, compound

HRID 1910696Notes

Reaction equation

Cl[C:2]1[C:3]2[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:4]=2[N:5]([CH3:21])[C:6](=[O:20])[CH:7]([CH2:9][C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=2)[N:8]=1.[OH:27][CH:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1.C(=O)([O-])[O-].[Na+].[Na+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.C(OCC)(=O)C>[Cl:26][C:24]1[CH:23]=[CH:22][C:4]2[N:5]([CH3:21])[C:6](=[O:20])[CH:7]([CH2:9][C:10]3[CH:19]=[CH:18][C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[CH:11]=3)[N:8]=[C:2]([N:31]3[CH2:32][CH2:33][CH:28]([OH:27])[CH2:29][CH2:30]3)[C:3]=2[CH:25]=1

Participants

Conditions

Temperature: 100 °C

Procedure

5,7-Dichloro-1-methyl-3-(naphthalen-2-ylmethyl)-1H-benzo[e][1,4]diazepin-2(3H)-one (0.36 g, 0.94 mmol), 4-hydroxypiperidine (0.38 g, 3.8 mmol), sodium carbonate (0.40 g, 3.8 mmol), and tetrabutylammonium iodide (0.09 g, 0.24 mmol) were combined in toluene (5 mL) and heated to 100° C. for 24 hours. The solution was cooled, diluted with ethyl acetate, washed with water, brine, dried with magnesium sulfate, filtered and concentrated in vacuo. Column chromatography eluting with a gradient of 25-100% ethyl acetate in hexanes provided 7-chloro-5-(4-hydroxypiperidin-1-yl)-1-methyl-3-(naphthalen-2-ylmethyl)-1H-benzo[e][1,4]diazepin-2(3H)-one. (35 mg, 8% yield) ESI m/z measured 448.1794 [M+H]+. calculated 448.1792.

Workup

temperatureThe solution was cooled
washwashed with water, brine
dry with materialdried with magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
washColumn chromatography eluting with a gradient of 25-100% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-89de6f8bcec74fd6a6afd97dab05fbba
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08604023B2

Reaction notes

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