Water → (3S)-N-(7-oxoazepan-4-yl)-1-phenylpiperidine-3-carboxamide

HRID 656347Notes

Reaction equation

[O:1]=[C:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:9]([C@H:11]2[CH2:16][CH2:15][CH2:14][N:13]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:12]2)=[O:10])[CH2:4][CH2:3]1.[N-:23]=[N+]=[N-].[Na+].O.[OH-].[Na+]>Cl>[O:1]=[C:2]1[NH:23][CH2:7][CH2:6][CH:5]([NH:8][C:9]([C@H:11]2[CH2:16][CH2:15][CH2:14][N:13]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:12]2)=[O:10])[CH2:4][CH2:3]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of (3S)-N-(4-oxocyclohexyl)-1-phenylpiperidine-3-carboxamide (10 mg, 0.00003 mol, prepared as example 171) in concentrated aqueous HCl (0.5 mL), was added sodium azide (2.27 mg, 0.0000350 mol) in small portions over 3 minutes with slow agitation. The temperature was slowly increased to 50° C. The reaction temperature was maintained at 50° C. for 8.5 h and then poured into 50 g of crushed ice and water. The solution was basified with cold 50% NaOH and the resulting solution was extracted with EtOAc(×3). The EtOAc extracts were combined, dried over MgSO4, filtered and evaporated to yield the crude product, which was purified by prep-HPLC. LCMS: (M+H)+=316.2.

Workup

customover 3 minutes
temperatureThe reaction temperature was maintained at 50° C. for 8.5 h
extractionthe resulting solution was extracted with EtOAc(×3)
dry with materialdried over MgSO4
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-2469ec55cb51436e9a4327f2865a2cab
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071624B2

Reaction notes

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