1,2-Dichloroethane → 3-(tert-Butyl)-5-(4-(4-chlorophenoxy)piperidine-1-carbonyl)benzamide

HRID 2170858Notes

Reaction equation

[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:14]([N:16]2[CH2:21][CH2:20][CH:19]([O:22][C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)[CH2:18][CH2:17]2)=[O:15])[CH:13]=1)[C:8](O)=[O:9])([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.C1C=CC2N(O)N=[N:40]C=2C=1.C(N(CC)C(C)C)(C)C.O.[NH4+]>CN(C)C=O.O>[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:14]([N:16]2[CH2:21][CH2:20][CH:19]([O:22][C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)[CH2:18][CH2:17]2)=[O:15])[CH:13]=1)[C:8]([NH2:40])=[O:9])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

To a stirred solution of 3-(tert-butyl)-5-(4-(4-chlorophenoxy)piperidine-1-carbonyl)benzoic acid (30 mg, 0.072 mmol, Step-1), EDC (21 mg, 0.11 mmol), HOBT (17 mg, 0.11 mmol), and N,N-diisopropylethylamine (0.28 mL, 1.61 mmol) in N,N-dimethylformamide (3 mL) was add 25% ammonium water (1 mL) at room temperature. After stirring at 60° C. for 2 hours, the mixture was poured into water (5 mL). This was extracted with ethyl acetate (5 mL) and washed with water (5 mL). The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica-gel column chromatography (NH-gel, eluting with ethyl acetate) and then preparative LC-MS to give 10.4 mg (35% yield) of the title compound.

Workup

extractionThis was extracted with ethyl acetate (5 mL)
washwashed with water (5 mL)
dry with materialThe organic layer was dried over sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica-gel column chromatography (NH-gel, eluting with ethyl acetate)

Sources & evidence

ORD record: ord-05d6885f07b44654aedb7be985f46c0c
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09051296B2

Reaction notes

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